18_page_(S)-1-Phenyl-2-propanol (P2Pol) [C9H12O] [CAS 1517-68-6; InChIKey WYTRYIUQUDTGSX-QMMMGPOBSA-

Query 1. Query

Query

Results

Date

RX.PXRN=2553541

90 reactions in Reaxys

2018-05-22 18h:44m:03s (UTC)

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O

HO

H

Rx-ID: 3756857 View in Reaxys 1/90 Yield

Conditions & References With secondary alcohol dehydrogenase from Thermoanaerobacter ethanolicus W110I mutant, nicotinamide adenine dinucleotide phosphate in isopropyl alcohol, Time= 6h, T= 50 °C , pH= 8, Enzymatic reaction, Reagent/catalyst, enantioselective reaction Patel, Jay M.; Musa, Musa M.; Rodriguez, Luis; Sutton, Dewey A.; Popik, Vladimir V.; Phillips, Robert S.; Organic and Biomolecular Chemistry; vol. 12; nb. 31; (2014); p. 5905 - 5910 View in Reaxys 4.4. Bioreduction of 1a-o by using Kluyveromyces marxianus growing cells: general procedure Kluyveromyces marxianus CBS 6556 was stored on agar slants at 4 °C. For inoculum preparation, a 250 mL conical ErlenMeyer flask containing 100 mL of yeast maintenance medium (YMM) (previously autoclaved at 121 °C, 1 atm, for 15 min), was inoculated with a single loopful of the microorganisms from the agar slants. The flask was then incubated aerobically at 30 °C in a rotary shaker at 200 rpm for 24 h. Next, the growing cultures were inoculated (5percent v/v) into a 250 mL conical ErlenMeyer flask containing 100 mL of YMM and incubated for additional 24 h under the same conditions. These cultures were then used as a final inoculum (1percent v/v) into a 1000 mL flask containing 400 mL of YMM. After 24 h of incubation at 30 °C in the shaker (200 rpm), a mixture of 100 mg of the ketone 1a-o dissolved in 1 mL of absolute ethanol was added. The reactions were monitored by GC, by collecting suspension aliquots of 1 mL after 1, 3, 4 and 5 days of reaction from each flask: after extraction with ethyl acetate (2 mL), the organic phase was analyzed by GC. After the appropriate conversion, the suspension was centrifuged (3000 rpm, 6 min, 4 °C), and the aqueous phase extracted with ethyl acetate (4 .x. 150 ml). The yellow organic phase was dried over Na2SO4, filtered and evaporated under reduced pressure. The residue was purified by silica gel column chromatography using petroleum ether and ethyl acetate (90:10 or 80:20) as eluent to yield the desired alcohols. [50] and [51] With Kluyveromyces marxianus CBS 6556 in ethanol, Time= 96h, T= 30 °C , Microbiological reaction, Yeast maintenance medium, Enzymatic reaction, optical yield given as percent ee, enantioselective reaction Vitale, Paola; Perna, Filippo Maria; Perrone, Maria Grazia; Scilimati, Antonio; Tetrahedron Asymmetry; vol. 22; nb. 23; (2011); p. 1985 - 1993 View in Reaxys With Tween 80, bakers' yeast, Sucrose, T= 25 - 32 °C Shi, Xiao-Xin; Yao, Jian-Zhong; Kang, Li; Shen, Chun-Li; Yi, Fei; Journal of Chemical Research; nb. 10; (2004); p. 681 683 View in Reaxys With baker’s yeast in water, Time= 24h, T= 37 °C Vitale, Paola; Abbinante, Vincenzo Mirco; Perna, Filippo Maria; Salomone, Antonio; Cardellicchio, Cosimo; Capriati, Vito; Advanced Synthesis and Catalysis; vol. 359; nb. 6; (2017); p. 1049 - 1057 View in Reaxys in water, Time= 3h, T= 30 °C , Geotrichum candidum IFO4597 on a diluted medium (glycerol, yeast extract, polypeptone) Nakamura, Kaoru; Matsuda, Tomoko; Ohno, Atsuyoshi; Tetrahedron Asymmetry; vol. 7; nb. 10; (1996); p. 3021 - 3024 View in Reaxys With 2-(N-morpholino)ethanesulfonic acidbuffer, NAD, isopropyl alcohol, Time= 20h, T= 30 °C , acetone powder of Geotrichum candidum Nakamura; Matsuda; Journal of Organic Chemistry; vol. 63; nb. 24; (1998); p. 8957 - 8964 View in Reaxys With n-hexan-2-ol, Geotrichum candidum IFO 4597 cells on BL-100 polymer in hexane, Time= 24h, T= 30 °C , Reduction Nakamura, Kaoru; Inoue, Yuko; Matsuda, Tomoko; Misawa, Ibuki; Journal of the Chemical Society - Perkin Transactions 1; nb. 16; (1999); p. 2397 - 2402 View in Reaxys

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4.4 General procedure for the catalytic, enantioselective reduction of prochiral ketones with precatalyst [Cp*Rh(bpy) (H2O)](OTf)2, sodium formate, and NAD+ biomimics, 1 or 3, in the presence of the HLADH enzyme General procedure: The reported reaction conditions, such as the reactant ratio, reaction temperature, and the pre-catalyst amount, were obtained after numerous trial tests; however, the reaction conditions were not optimized. For reaction temperatures tested, from RT to 39°C, while 30°C exhibited the highest ee (85percent–99percent) for the chiral alcohol products. A general reaction procedure is given as follows, by using NAD+ biomimic, 1, and substrate, PhCH2CH2COCH3, 7, as an example: [Cp*Rh(bpy)(H2O)](OTf)2 (1.90mg, 2.61×10−3mmol), sodium formate (17.80mg, 261.69×10−3mmol), NAD+ biomimic, 1, (4.10mg, 11.32×10−3mmol), and HLADH (23.80mg, 10.23 units) were placed in a 10mL Schlenk flask capped with a septum, and Schlenk techniques were carefully followed to deoxygenate the solid mixture. Potassium phosphate buffer (5mL, 100mM, pH=7.02, de-O2) was added to give a clear solution, followed by the addition of the ketone substrate (12.5μL, 83.41×10−3mmol, de-O2) via syringe, respectively. Under a gentle N2 pressure, the septum was removed, and the reaction flask was capped with a glass-stopper sealed with a small amount of grease and a metal clip. The stopcock of the reaction flask to N2 gas was then shut, and the reaction flask was immediately shaken in a water-bath shaker at 30°C, with the water level above the reaction mixture solution. The reaction was monitored by means of GC for 24h (yield, 90percent; 93percent ee). Small amounts of a precipitate were observed in all reactions tested after 24h. The SDS-PAGE analysis indicated the observed precipitate to be mainly the HLADH enzyme.

With [(η5-C5Me5)Rh(2,2'-bipyridyl)(H2O)](OTf)2, horse liver alcohol dehydrogenase, sodium formate, N-1-benzylnicotinamide triflate in aq. phosphate buffer, Time= 24h, T= 30 °C , pH= 7.02, Schlenk technique, Inert atmosphere, Enzymatic reaction, Catalytic behavior, Reagent/catalyst, enantioselective reaction Lo, H. Christine; Ryan, Jessica D.; Kerr, John B.; Clark, Douglas S.; Fish, Richard H.; Journal of Organometallic Chemistry; vol. 839; (2017); p. 38 - 52 View in Reaxys 2.6.3. Bioreduction of ketones 1a–d on preparative scale General procedure: Lyophilized cell powder (1500 mg) was suspended in phosphatebuffer (25 mL, 100 mM, pH 7.5) containing one of the ketones 1a, 1b,1c or 1d (100 mg) and glucose (4 w/vpercent) in 20 mL Erlenmeyer-flasks.The mixture was shaken on an orbital shaker (150 rpm) at 30C for24 h. Then the mixture was extracted with ethyl acetate (50 mL)dried over Na2SO4and concentrated under reduced pressure. Theresidue was purified by plate chromatography (silica gel, eluent:hexane – ethyl acetate 10:4) to yield the corresponding secondaryalcohol (S)-2a-d.

With D-glucose in aq. phosphate buffer, Time= 24h, T= 30 °C , pH= 7.5, Enzymatic reaction, Reagent/catalyst, Temperature, Solvent, pH-value, stereoselective reaction Bódai, Viktória; Nagy-Győr, László; Örkényi, Róbert; Molnár, Zsófia; Kohári, Szabolcs; Erdélyi, Balázs; Nagymáté, Zsuzsanna; Romsics, Csaba; Paizs, Csaba; Poppe, László; Hornyánszky, Gábor; Journal of Molecular Catalysis B: Enzymatic; vol. 134; (2016); p. 206 - 214 View in Reaxys 4 : Example 4 WASHEDPHASEOLUS AUREUS L (GREEN grams) 50 g. were taken into a conical flask and allowed to soak in deionised water (400 ml) for a period of 24 hr. Phenylacetone (0.500 g; 0.0037 moles) I (d) was added to the SOAKEDPHASEOLUS AUREUS L (green grams) in the above water, covered and allowed to shake for 24 hr at 15-20 °C. Then the green grams were filtered off and washed with deionised water (3 x 100 ml). The combined filtrate was extracted with chloroform (3 x 500 ml).

The chloroform layer was dried and the crude product obtained (330 MG). Pure 1-PHENYL-(2S)-PROPAN-2-OL II (d) was obtained after column chromatography with silica gel using chloroform as eluent. Yield: 0.232 g, 45.67percent ; ee: 97.86percent ; ([OC] 25D = +32. 62°, C= 1, chloroform).

With water, Phaseolus aureus L (green grams), Time= 24h, T= 15 - 20 °C , Enzymatic reaction Patent; COUNCIL OF SCIENTIFIC AND INDUSTRIAL RESEARCH; WO2004/87629; (2004); (A1) English View in Reaxys in ethanol, bakers' yeast in glucose solution Fronza; Fuganti; Grasselli; Mele; Journal of Organic Chemistry; vol. 56; nb. 21; (1991); p. 6019 - 6023 View in Reaxys With formate dehydrogenase, NAD, sodium formate, alcohol dehydrogenase in hexane, water Kruse, Wolfgang; Hummel, Werner; Kragl, Udo; Recueil des Travaux Chimiques des Pays-Bas-Journal of the Royal Netherlands; vol. 115; nb. 4; (1996); p. 239 - 243

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View in Reaxys With sodium formate, nicotinamide adenine dinucleotide, [CpRh(bpy)(H2O)]OTf2 in phosphate buffer, pH= 7.02 Lo, H. Christine; Fish, Richard H.; Angewandte Chemie - International Edition; vol. 41; nb. 3; (2002); p. 478 - 481 View in Reaxys With Cyclopentanol, dried cells of Geotrichum candidum IFO 4597 (APG4), NADP, Time= 20h, T= 30 °C , pH= 7.0, Enzymatic reaction, Reduction Matsuda, Tomoko; Harada, Tadao; Nakajima, Nobuyoshi; Itoh, Toshiyuki; Nakamura, Kaoru; Journal of Organic Chemistry; vol. 65; nb. 1; (2000); p. 157 - 163 View in Reaxys Reaction Steps: 2 1: 90 percent / SO2Cl2 / CCl4 / 40 °C 2: 24 h / Bakers' yeast With sulfuryl dichloride in tetrachloromethane Besse; Renard; Veschambre; Tetrahedron Asymmetry; vol. 5; nb. 7; (1994); p. 1249 - 1268 View in Reaxys Typical preparative scalereactions using TbSADH best mutant General procedure: A test tube (10 mL)containing LB (4 mL) and kanamycin (50 µg/mL) was inoculated with mutant SZ2074 and incubated 8h (37°C, 220 rpm). The pre-culture was then inoculated intoTB (400 mL) containing kanamycin (50 µg/mL) and allowed to grow at 37°C until O.D.was ca. 0.6. IPTG was then added to a final concentration of 0.2 mM and theculture was grown for 16 h (30°C, 180 rpm). Cells were pelleted bycentrifugation, washed once with pH=7.4 potassium phosphate buffer (100 mM) andthen resuspended in pH=7.4 potassium phosphate buffer (45 mL, 100 mM). Cellswere then transferred to a 50 mL Erlenmeyer flask and 1.4 mg/mL lysozyme (70mg), 6U DNase I (50 µL), NADP+ 100mM (200 µL) were added. Substrate 3a (30 mM) in 10percent isopropanol (5 mL)was then added. Biotransformation was carried out at 30°C, 220rpm. GC controlindicated a 92percent conversion after 4h. The reaction was stopped after 6h when theconversion was 94percent. The organic phase was extracted with ethyl acetate (3x100mL) and crude reaction product was purified using column chromatography. (EA:PE1:4, Rf=0.55) afforded (R)-4a as a colourless liquid (157 mg,yield=75percent).

With alcohol dehydrogenase TbSADH from Thermoanaerobacter brockii W110L mutant in aq. phosphate buffer, isopropyl alcohol, T= 30 °C , Enzymatic reaction, Reagent/catalyst, enantioselective reaction Sun, Zhoutong; Li, Guangyue; Ilie, Adriana; Reetz, Manfred T.; Tetrahedron Letters; vol. 57; nb. 32; (2016); p. 3648 - 3651 View in Reaxys With halophilic alcohol dehydrogenase ADH2 from Haloferax volcanii, NADPH in ethanol, acetonitrile, T= 25 °C , pH= 8, Enzymatic reaction, enantioselective reaction Alsafadi, Diya; Alsalman, Safaa; Paradisi, Francesca; Organic and Biomolecular Chemistry; vol. 15; nb. 43; (2017); p. 9169 - 9175 View in Reaxys With W110V mutated thermoanaerobacter pseudoethanolicus secondary alcohol dehydrogenase, nicotinamide adenine dinucleotide phosphate, isopropyl alcohol in aq. buffer, T= 50 °C , pH= 8, Enzymatic reaction, enantioselective reaction Musa, Musa M.; Bsharat, Odey; Karume, Ibrahim; Vieille, Claire; Takahashi, Masateru; Hamdan, Samir M.; European Journal of Organic Chemistry; vol. 2018; nb. 6; (2018); p. 798 - 805 View in Reaxys

O

HO

HO

H

H

Rx-ID: 3756858 View in Reaxys 2/90 Yield 69 %

Conditions & References With methanesulfonic acid, (R,R)-dihydroborate in hexane, Time= 48h, T= -20 °C , Title compound not separated from byproducts

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Imai, Toshiro; Tamura, Tadashi; Yamamuro, Akira; Sato, Tsuneo; Wollmann, Theodor A.; et al.; Journal of the American Chemical Society; vol. 108; nb. 23; (1986); p. 7402 - 7404 View in Reaxys With nicotinamide adenine dinucleotide, rat liver homogenate supernatant, T= 37 °C , other catalysts, Product distribution Prelusky; Coutts; Pasutto; Journal of Pharmaceutical Sciences; vol. 71; nb. 12; (1982); p. 1390 - 1393 View in Reaxys With lithium aluminium tetrahydride, crowned 2,2'-dihydroxy-1,1'-binaphthyl (S,S)-4 in tetrahydrofuran, Time= 24h, T= 0 °C , Yield given. Yields of byproduct given. Title compound not separated from byproducts Yamamoto, Koji; Ueno, Koji; Naemura, Koichiro; Journal of the Chemical Society, Perkin Transactions 1: Organic and BioOrganic Chemistry (1972-1999); nb. 4; (1991); p. 2607 - 2608 View in Reaxys With water, isopropyl alcohol, T= 30 °C , resting cells of Sulfolobus solfataricus, pH 5.0, Title compound not separated from byproducts Trincone, Antonio; Nicolaus, Barbara; Lama, Licia; Gambacorta, Agata; Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry; vol. 32; nb. 1; (1993); p. 25 - 29 View in Reaxys With (S)-oxazaborolidine, borane in tetrahydrofuran, Time= 0.166667h, T= 25 °C , Yield given. Yields of byproduct given. Title compound not separated from byproducts Kim, Yong Hae; Park, Doo Han; Byun, Il Suk; Yoon, I. K.; Park, C. S.; Journal of Organic Chemistry; vol. 58; nb. 17; (1993); p. 4511 - 4512 View in Reaxys With dimethylsulfide borane complex, (R)-B-methyl-4,5,5-triphenyl-1,3,2-oxazaborolidine in tetrahydrofuran, T= 0 °C , Title compound not separated from byproducts Berenguer; Garcia; Vilarrasa; Tetrahedron Asymmetry; vol. 5; nb. 2; (1994); p. 165 - 168 View in Reaxys With diisobutylaluminium hydride, (S)-1-methyl-2-lt;(piperidin-1-yl)-methylgt;pyrrolidine, tin(ll) chloride in dichloromethane, Time= 0.166667h, T= -100 °C , Yield given. Yields of byproduct given Oriyama, Takeshi; Mukaiyama, Teruaki; Chemistry Letters; (1984); p. 2071 - 2074 View in Reaxys With borane-THF, L-proline in toluene, Time= 0.25h, Heating, Yield given. Yields of byproduct given. Title compound not separated from byproducts Brunel, Jean Michel; Maffei, Michel; Buono, Gerard; Tetrahedron: Asymmetry; vol. 4; nb. 10; (1993); p. 2255 - 2260 View in Reaxys With dimethylsulfide borane complex, chiral oxazaphospholidine oxide in tetrahydrofuran, T= 60 °C , Yield given. Yields of byproduct given Chiodi, Olivier; Fotiadu, Frederic; Sylvestre, Maud; Buono, Gerard; Tetrahedron Letters; vol. 37; nb. 1; (1996); p. 39 - 42 View in Reaxys With D-glucose, Zygosaccharomyces rouxii cells in water, Time= 1h, T= 28 °C Erdelyi, Balazs; Szabo, Antal; Seres, Gabor; Birincsik, Laszlo; Ivanics, Jozsef; Szatzker, Gabor; Poppe, Laszlo; Tetrahedron Asymmetry; vol. 17; nb. 2; (2006); p. 268 - 274 View in Reaxys With Geotrichum candidum IFO 4597 in water, Time= 24h, T= 30 °C , Microbiological reaction, Reduction, Product distribution, Further Variations: Reagents Nakamura, Kaoru; Fujii, Mikio; Ida, Yoshiteru; Journal of the Chemical Society, Perkin Transactions 1; nb. 19; (2000); p.

3205 - 3211 View in Reaxys

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With NADP, isopropyl alcohol in hexane, Time= 12h, T= 50 °C , Enzymatic reaction, Product distribution, Further Variations: Solvents Musa, Musa M.; Ziegelmann-Fjeld, Karla I.; Vieille, Claire; Zeikus, J. Gregory; Phillips, Robert S.; Angewandte Chemie International Edition; vol. 46; nb. 17; (2007); p. 3091 - 3094 View in Reaxys With nicotinamide adenine dinucleotide phosphate, tris hydrochloride, isopropyl alcohol in water, acetonitrile, Time= 24h, T= 50 °C , stereoselective reaction Musa, Musa M.; Ziegelmann-Fjeld, Karla I.; Vieille, Claire; Phillips, Robert S.; Organic and Biomolecular Chemistry; vol.

6; nb. 5; (2008); p. 887 - 892 View in Reaxys With ECOENG500, [RuCl(p-cymene)TsDPEN], water, sodium formate, T= 20 - 50 °C , optical yield given as percent ee Hut'ka, Martin; Toma, Stefan; Monatshefte fur Chemie; vol. 139; nb. 7; (2008); p. 793 - 798 View in Reaxys With dimethylsulfide borane complex, (S)-1-methyl-3,3-diphenyl-hexahydropyrrolo[1,2-c][1,3,2]oxazaborole in tetrahydrofuran, Time= 14.5h, T= 30 °C , optical yield given as percent ee, enantioselective reaction Ema, Tadashi; Ura, Norichika; Yoshii, Masataka; Korenaga, Toshinobu; Sakai, Takashi; Tetrahedron; vol. 65; nb. 46; (2009); p. 9583 - 9591 View in Reaxys Stage 1: With phenylsilane, copper diacetate, (S)-4-phenyl-4,5-dihydro-3H-dinaphtholt;2,1-c;1',2'-egt;phosphepine in toluene, Time= 5h, T= -20 °C , Inert atmosphere Stage 2: With methanol, tetrabutyl ammonium fluoride in tetrahydrofuran, Time= 2h, optical yield given as percent ee, enantioselective reaction Junge, Kathrin; Wendt, Bianca; Addis, Daniele; Zhou, Shaolin; Das, Shoubhik; Beller, Matthias; Chemistry - A European Journal; vol. 16; nb. 1; (2010); p. 68 - 73 View in Reaxys General procedure for catalytic reductions: General procedure: In a Schlenk tube, dichloro-p-cymene ruthenium dimer (15.5 mg, 0.025 mmol) and ligand (0.05 mmol) were dissolved in water (4 mL) at 30°C and stirred during 1h. Sodium formate (0.68 mg, 10 mmol) and substrate (1 mmol) were then added. The reaction mixture was maintained at 30°C until total reduction of the ketone (monitored by GC). Alcohol was extracted with pentane (3x10 mL), dried over MgSO4 and evaporated under reduced pressure. The product was purified by thin layer chromatography with petroleum ether/ethyl acetate mixture, and spectral data compared with the literature[ii]. Enantiomeric excesses were determined by GC on chiral column.

With (p-cymene)ruthenium(II) chloride, water, sodium formate, (2S)-N-phenylpyrrolidine-2-carboxamide, Time= 17h, T= 30 °C , Inert atmosphere, optical yield given as percent ee, enantioselective reaction Boukachabia, Mourad; Zeror, Saoussen; Collin, Jacqueline; Fiaud, Jean-Claude; Zouioueche, Louisa Aribi; Tetrahedron Letters; vol. 52; nb. 13; (2011); p. 1485 - 1489 View in Reaxys Reaction Steps: 2 1.1: iron(II) acetate; 1,2-bis((2S,5S)-2,5-dimethylphospholano)benzene / tetrahydrofuran / 65 °C / Inert atmosphere 1.2: 42 h / 20 °C / Inert atmosphere 2.1: water; sodium hydroxide / tetrahydrofuran; methanol / 0 - 20 °C / Inert atmosphere With water, iron(II) acetate, 1,2-bis((2S,5S)-2,5-dimethylphospholano)benzene, sodium hydroxide in tetrahydrofuran, methanol Addis, Daniele; Shaikh, Nadim; Zhou, Shaolin; Das, Shoubhik; Junge, Kathrin; Beller, Matthius; Chemistry - An Asian Journal; vol. 5; nb. 7; (2010); p. 1687 - 1691 View in Reaxys Stage 1: With diethylzinc, 2,6-bis((R)-4-phenyl-4,5-dihydrooxazol-2-yl)pyridine in tetrahydrofuran, toluene, Time= 20h, T= 20 °C , Inert atmosphere Stage 2: With sodium hydroxide in tetrahydrofuran, methanol, diethyl ether, toluene, Time= 0.5h, Inert atmosphere, optical yield given as percent ee, enantioselective reaction

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Junge, Kathrin; Moeller, Konstanze; Wendt, Bianca; Das, Shoubhik; Goerdes, Dirk; Thurow, Kerstin; Beller, Matthias; Chemistry - An Asian Journal; vol. 7; nb. 2; (2012); p. 314 - 320 View in Reaxys 25 :General procedure: The hydrogenation substrate (20 mmol), the base (as in Table 2), iso-propanol (10 ml), and the catalyst precursor RuCl2(L4) (0.01 mmol) were placed into a pressure reactor and stirred under H2 (50 bar) at the given temperature for the given amount of time as indicated in Table 2.

With RuCl2((R,R)-N,N'-bis(2-(tert-butylthio)-4-tert-butylbenzylidene)-1,2-diaminocyclohexane), hydrogen, potassium hydoxide in isopropyl alcohol, Time= 2.5h, T= 60 °C , p= 37503.8Torr , Inert atmosphere, Autoclave, Temperature, Reagent/catalyst, Overall yield = 99 percentChromat.; Optical yield = 40 percent ee Patent; FIRMENICH SA; Santoro, Francesco; Saudan, Lionel; Saudan, Christophe; US2013/274487; (2013); (A1) English View in Reaxys 11 : Example 11: Application of chiral spiro-pyridylamidophosphine ligand (R)-Ii (prepared in Example 9) in the asymmetric catalytic hydrogenation reaction of carbonyl compounds Example 11: Application of chiral spiro-pyridylamidophosphine ligand (R)-Ii (prepared in Example 9) in the asymmetric catalytic hydrogenation reaction of carbonyl compounds[0059] [0060] Under the protection of nitrogen atmosphere, 0.5 mg (0.74µmol) [Ir(COD)]Cl2, 1.2 mg (1.6µmol) (R)-Ii were added to the inner hydrogenation tube. Subsequently, 1 ml absolute ethyl alcohol was added and stirred for 1 h at room temperature. The inner reaction tube was placed into the hydrogenation reactor.

After substitution by hydrogen, the reaction was stirred for 1 h at a hydrogen pressure of 1 atmosphere. The reactor was opened, and 7.5-150 mmol substrate (solid substrate, added after dissolved by ethanol) was added, followed by 0.05-25 mmol potassium tert-butoxide solution in ethanol (0.5 ml (0.1 mmol/mL)-25 ml (1 mmol/mL)) added with a syringe. The reactor was sealed, and hydrogen was filled to a pressure of 8-10 atm, and the reaction was stirred under the hydrogen pressure at room temperature for a while ranging from 10 minutes to 24 hours. After the hydrogenation was finished, the reaction solution was filtered through a short silica gel column to remove the catalyst, and the conversion rate and yield of the reaction were analyzed by gas chromatography or nuclear magnetic resonance (NMR); and the optical purity of the product was analyzed by gas chromatography or high performance liquid chromatography. The results of the hydrogenation experiments were listed in Table 1.

With bis(1,5-cyclooctadiene)diiridium(I) dichloride, (R)-N-(3-methylpyridyl-2-methyl)-7-di-(3,5-di-tert-butylphenyl)phosphino-7'-amino-1,1'-spiro-dihydro-indene, potassium tert-butylate, hydrogen in ethanol, Time= 3h, T= 20 °C , p= 6080.41 7600.51Torr , Inert atmosphere, Sealed tube, Overall yield = 100 percent Patent; Zhejiang Jiuzhou Pharma Science and Technology Co., Ltd.; ZHOU, Qilin; XIE, Jianhua; LIU, Xiaoyan; XIE, Jianbo; WANG, Lixin; EP2641910; (2013); (A1) English View in Reaxys Asymmetric Reduction of Acetophenone with Catalyst 1;Typical Procedure General procedure: A 100 mL, flame-dried, two-necked, round-bottomed flaskequipped with a magnetic stirrer bar, was charged withcatalyst 1 (0.4 mmol) and anhyd THF (4 mL). BH3·THF (2.4mmol, 1.2 equiv) was added under argon from a syringe. Asoln of PhCOMe (2 mmol, 0.22 mL) in anhyd THF (2 mL)was added dropwise at 1 mL/h and the solution was thenstirred at r.t. under argon for 18 h. When the reaction wascomplete, the mixture was hydrolyzed by the addition ofMeOH (5 mL) and 1 M aq HCl (5 mL) and stirred for 30 min.The mixture was then extracted with Et2O (3 × 50 mL), and the combined organic extracts were dried (MgSO4) andconcentrated under reduced pressure. The residual crudeproduct was purified by column chromatography [silica gel,EtOAc–hexanes (1:3)] to give enantiomerically enriched1-phenylethanol as a colorless oil; yield: 0.17 g (70percent).

With borane-THF, (2R)-2-amino-2-phenylethanol N-borane in tetrahydrofuran, Time= 18h, T= 20 °C , Inert atmosphere, Overall yield = 60 percent; enantioselective reaction Pinaka, Afroditi; Dimotikali, Dimitra; Chankvetadze, Bezhan; Papadopoulos, Kyriakos; Vougioukalakis, Georgios C.; Synlett; vol. 24; nb. 18; (2013); p. 2401 - 2406; Art.No: ST-2013-B0829-L View in Reaxys With secondary alcohol dehydrogenase from Thermoanaerobacter ethanolicus W110A mutant, nicotinamide adenine dinucleotide phosphate in isopropyl alcohol, Time= 6h, T= 50 °C , pH= 8, Enzymatic reaction, enantioselective reaction Patel, Jay M.; Musa, Musa M.; Rodriguez, Luis; Sutton, Dewey A.; Popik, Vladimir V.; Phillips, Robert S.; Organic and Biomolecular Chemistry; vol. 12; nb. 31; (2014); p. 5905 - 5910 View in Reaxys

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11 : Example 11 Application of Chiral Spiro-Pyridylamidophosphine Ligand (R)-Ii (Prepared in Example 9) in the Asymmetric Catalytic Hydrogenation Reaction of Carbonyl Compounds Example 11 Application of Chiral Spiro-Pyridylamidophosphine Ligand (R)-Ii (Prepared in Example 9) in the Asymmetric Catalytic Hydrogenation Reaction of Carbonyl Compounds Under the protection of nitrogen atmosphere, 0.5 mg (0.74 gmol) [Ir(COD)]Cl2, 1.2 mg (1.6 μmol) (R)-Ii were added to the inner hydrogenation tube. Subsequently, 1 ml absolute ethyl alcohol was added and stirred for 1 h at room temperature. The inner reaction tube was placed into the hydrogenation reactor. After substitution by hydrogen, the reaction was stirred for 1 h at a hydrogen pressure of 1 atmosphere. The reactor was opened, and 7.5-150 mmol substrate (solid substrate, added after dissolved by ethanol) was added, followed by 0.05-25 mmol potassium tertbutoxide solution in ethanol (0.5 ml (0.1 mmol/mL)-25 ml (1 mmol/mL)) added with a syringe. The reactor was sealed, and hydrogen was filled to a pressure of 8-10 atm, and the reaction was stirred under the hydrogen pressure at room temperature for a while ranging from 10 minutes to 24 hours. After the hydrogenation was finished, the reaction solution was filtered through a short silica gel column to remove the catalyst, and the conversion rate and yield of the reaction were analyzed by gas chromatography or nuclear magnetic resonance (NMR); and the optical purity of the product was analyzed by gas chromatography or high performance liquid chromatography. The results of the hydrogenation experiments were listed in Table 1.

With bis(1,5-cyclooctadiene)diiridium(I) dichloride, (R)-N-(3-methylpyridyl-2-methyl)-7-di-(3,5-di-tert-butylphenyl)phosphino-7'-amino-1,1'-spiro-dihydro-indene, potassium tert-butylate, hydrogen in ethanol, Time= 3h, T= 20 °C , p= 6080.41 7600.51Torr , Autoclave, Overall yield = 100percent; Optical yield = 25percent ee Patent; Zhejiang Jiuzhou Pharma Science and Technology Co., Ltd.; Zhou, Qilin; Xie, Jianhua; Liu, Xiaoyan; Xie, Jianbo; Wang, Lixin; US8962839; (2015); (B2) English View in Reaxys Stage 1: With diethoxymethylane, C36H31FeN3O3 in toluene, Time= 6h, T= -78 - 20 °C , Schlenk technique, Inert atmosphere Stage 2: With potassium carbonate in methanol, Time= 1h, T= 20 °C , Schlenk technique, Inert atmosphere, enantioselective reaction Bleith, Tim; Wadepohl, Hubert; Gade, Lutz H.; Journal of the American Chemical Society; vol. 137; nb. 7; (2015); p. 2456 2459 View in Reaxys 2.2.2. General procedure for mutant TeSADH-catalyzed racemization General procedure: Enantiopure alcohol (0.015 mmol), NADP+ (0.5 mg), NADPH (1.0 mg), mutant TeSADH (0.2 mg in Tris– HCl buffer solution, 50 mM, pH 8.0), Tris–HCl buffer solution (950 μL, 50 mM, pH 8.0), and acetonitrile (50 μL) were mixed in a 1.5-mL plastic tube. The reaction mixture was shaken at 50 °C and 200 rpm for 48 h, followed by extraction with ethyl acetate (2 × 500 μL). The combined organic layer was dried with sodium sulfate and concentrated to dryness. The remaining residue was treated with pyridine (two drops) and acetic anhydride (one drop) for 1 h to convert the alcohols to their corresponding acetates. The acetate products were diluted with CHCl3 prior to analysis on a GC equipped with a chiral column to determine ee.

With NADPH, nicotinamide adenine dinucleotide phosphate, W110A TeSADH in acetonitrile, T= 50 °C , pH= 8, Enzymatic reaction Musa, Musa M.; Patel, Jay M.; Nealon, Christopher M.; Kim, Chang Sup; Phillips, Robert S.; Karume, Ibrahim; Journal of Molecular Catalysis B: Enzymatic; vol. 115; (2015); p. 155 - 159 View in Reaxys 2.2.2. General procedure for mutant TeSADH-catalyzed racemization General procedure: Enantiopure alcohol (0.015 mmol), NADP+ (0.5 mg), NADPH (1.0 mg), mutant TeSADH (0.2 mg in Tris– HCl buffer solution, 50 mM, pH 8.0), Tris–HCl buffer solution (950 μL, 50 mM, pH 8.0), and acetonitrile (50 μL) were mixed in a 1.5-mL plastic tube. The reaction mixture was shaken at 50 °C and 200 rpm for 48 h, followed by extraction with ethyl acetate (2 × 500 μL). The combined organic layer was dried with sodium sulfate and concentrated to dryness. The remaining residue was treated with pyridine (two drops) and acetic anhydride (one drop) for 1 h to convert the alcohols to their corresponding acetates. The acetate products were diluted with CHCl3 prior to analysis on a GC equipped with a chiral column to determine ee.

With NADPH, nicotinamide adenine dinucleotide phosphate, W110G TeSADH in acetonitrile, T= 50 °C , pH= 8, Enzymatic reaction Musa, Musa M.; Patel, Jay M.; Nealon, Christopher M.; Kim, Chang Sup; Phillips, Robert S.; Karume, Ibrahim; Journal of Molecular Catalysis B: Enzymatic; vol. 115; (2015); p. 155 - 159 View in Reaxys With Thermoanaerobacter ethanolicus secondary alcohol dehydrogenase W110A mutant, NADP in isopropyl alcohol, acetone, Time= 24h, T= 50 °C , pH= 8, Enzymatic reaction, enantioselective reaction

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Karume, Ibrahim; Takahashi, Masateru; Hamdan, Samir M.; Musa, Musa M.; ChemCatChem; vol. 8; nb. 8; (2016); p.

1459 - 1463 View in Reaxys With Thermoanaerobacter ethanolicus secondary alcohol dehydrogenase W110G mutant, NADP in isopropyl alcohol, acetone, Time= 24h, T= 50 °C , pH= 8, Enzymatic reaction, enantioselective reaction Karume, Ibrahim; Takahashi, Masateru; Hamdan, Samir M.; Musa, Musa M.; ChemCatChem; vol. 8; nb. 8; (2016); p.

1459 - 1463 View in Reaxys Typical preparative scalereactions using TbSADH best mutant General procedure: A test tube (10 mL)containing LB (4 mL) and kanamycin (50 µg/mL) was inoculated with mutant SZ2074 and incubated 8h (37°C, 220 rpm). The pre-culture was then inoculated intoTB (400 mL) containing kanamycin (50 µg/mL) and allowed to grow at 37°C until O.D.was ca. 0.6. IPTG was then added to a final concentration of 0.2 mM and theculture was grown for 16 h (30°C, 180 rpm). Cells were pelleted bycentrifugation, washed once with pH=7.4 potassium phosphate buffer (100 mM) andthen resuspended in pH=7.4 potassium phosphate buffer (45 mL, 100 mM). Cellswere then transferred to a 50 mL Erlenmeyer flask and 1.4 mg/mL lysozyme (70mg), 6U DNase I (50 µL), NADP+ 100mM (200 µL) were added. Substrate 3a (30 mM) in 10percent isopropanol (5 mL)was then added. Biotransformation was carried out at 30°C, 220rpm. GC controlindicated a 92percent conversion after 4h. The reaction was stopped after 6h when theconversion was 94percent. The organic phase was extracted with ethyl acetate (3x100mL) and crude reaction product was purified using column chromatography. (EA:PE1:4, Rf=0.55) afforded (R)-4a as a colourless liquid (157 mg,yield=75percent).

With alcohol dehydrogenase TbSADH from Thermoanaerobacter brockii A85V/I86L/W110Q/L294Q mutant in aq. phosphate buffer, isopropyl alcohol, T= 30 °C , Enzymatic reaction, Reagent/catalyst, enantioselective reaction Sun, Zhoutong; Li, Guangyue; Ilie, Adriana; Reetz, Manfred T.; Tetrahedron Letters; vol. 57; nb. 32; (2016); p. 3648 - 3651 View in Reaxys Typical preparative scalereactions using TbSADH best mutant General procedure: A test tube (10 mL)containing LB (4 mL) and kanamycin (50 µg/mL) was inoculated with mutant SZ2074 and incubated 8h (37°C, 220 rpm). The pre-culture was then inoculated intoTB (400 mL) containing kanamycin (50 µg/mL) and allowed to grow at 37°C until O.D.was ca. 0.6. IPTG was then added to a final concentration of 0.2 mM and theculture was grown for 16 h (30°C, 180 rpm). Cells were pelleted bycentrifugation, washed once with pH=7.4 potassium phosphate buffer (100 mM) andthen resuspended in pH=7.4 potassium phosphate buffer (45 mL, 100 mM). Cellswere then transferred to a 50 mL Erlenmeyer flask and 1.4 mg/mL lysozyme (70mg), 6U DNase I (50 µL), NADP+ 100mM (200 µL) were added. Substrate 3a (30 mM) in 10percent isopropanol (5 mL)was then added. Biotransformation was carried out at 30°C, 220rpm. GC controlindicated a 92percent conversion after 4h. The reaction was stopped after 6h when theconversion was 94percent. The organic phase was extracted with ethyl acetate (3x100mL) and crude reaction product was purified using column chromatography. (EA:PE1:4, Rf=0.55) afforded (R)-4a as a colourless liquid (157 mg,yield=75percent).

With alcohol dehydrogenase TbSADH from Thermoanaerobacter brockii I86N mutant in aq. phosphate buffer, isopropyl alcohol, T= 30 °C , Enzymatic reaction, Reagent/catalyst, enantioselective reaction Sun, Zhoutong; Li, Guangyue; Ilie, Adriana; Reetz, Manfred T.; Tetrahedron Letters; vol. 57; nb. 32; (2016); p. 3648 - 3651 View in Reaxys With D-glucose in isopropyl alcohol, Time= 6h, T= 30 °C , pH= 7.5, Enzymatic reaction, Solvent, Reagent/catalyst, stereoselective reaction Bódai, Viktória; Nagy-Győr, László; Örkényi, Róbert; Molnár, Zsófia; Kohári, Szabolcs; Erdélyi, Balázs; Nagymáté, Zsuzsanna; Romsics, Csaba; Paizs, Csaba; Poppe, László; Hornyánszky, Gábor; Journal of Molecular Catalysis B: Enzymatic; vol. 134; (2016); p. 206 - 214 View in Reaxys With D-fructose, choline chloride, Time= 144h, T= 37 °C , Reagent/catalyst, Solvent, Overall yield = 88 percent Vitale, Paola; Abbinante, Vincenzo Mirco; Perna, Filippo Maria; Salomone, Antonio; Cardellicchio, Cosimo; Capriati, Vito; Advanced Synthesis and Catalysis; vol. 359; nb. 6; (2017); p. 1049 - 1057 View in Reaxys With choline chloride in water, glycerol, Time= 120h, T= 37 °C , Reagent/catalyst, Overall yield = 20 percent

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Vitale, Paola; Abbinante, Vincenzo Mirco; Perna, Filippo Maria; Salomone, Antonio; Cardellicchio, Cosimo; Capriati, Vito; Advanced Synthesis and Catalysis; vol. 359; nb. 6; (2017); p. 1049 - 1057 View in Reaxys With E. coli lyophilized alcohol dehydrogenase from Thermoanaerobacter ethanolicus I86A W110A variant, nicotinamide adenine dinucleotide phosphate in isopropyl alcohol, Time= 16h, T= 30 °C , pH= 7, Enzymatic reaction, enantioselective reaction Knaus, Tanja; Cariati, Luca; Masman, Marcelo F; Mutti, Francesco G.; Organic and Biomolecular Chemistry; vol. 15; nb.

39; (2017); p. 8313 - 8325 View in Reaxys With E. coli lyophilized alcohol dehydrogenase from Thermoanaerobacter ethanolicus W110A variant, nicotinamide adenine dinucleotide phosphate in isopropyl alcohol, Time= 16h, T= 30 °C , pH= 7, Enzymatic reaction, Reagent/catalyst, enantioselective reaction Knaus, Tanja; Cariati, Luca; Masman, Marcelo F; Mutti, Francesco G.; Organic and Biomolecular Chemistry; vol. 15; nb.

39; (2017); p. 8313 - 8325 View in Reaxys With NADP, alcohol dehydrogenase, Enzymatic reaction, stereoselective reaction Qu, Ge; Lonsdale, Richard; Yao, Peiyuan; Li, Guangyue; Liu, Beibei; Reetz, Manfred T.; Sun, Zhoutong; ChemBioChem; vol. 19; nb. 3; (2018); p. 239 - 246 View in Reaxys With DL-dithiothreitol, W110A/I86A double mutated thermoanaerobacter pseudoethanolicus secondary alcohol dehydrogenase, nicotinamide adenine dinucleotide phosphate, isopropyl alcohol, zinc(II) chloride in aq. buffer, T= 50 °C , pH= 8, Enzymatic reaction, enantioselective reaction Musa, Musa M.; Bsharat, Odey; Karume, Ibrahim; Vieille, Claire; Takahashi, Masateru; Hamdan, Samir M.; European Journal of Organic Chemistry; vol. 2018; nb. 6; (2018); p. 798 - 805 View in Reaxys With W110A mutated thermoanaerobacter pseudoethanolicus secondary alcohol dehydrogenase, nicotinamide adenine dinucleotide phosphate, isopropyl alcohol in aq. buffer, T= 50 °C , pH= 8, Enzymatic reaction, Reagent/catalyst, enantioselective reaction Musa, Musa M.; Bsharat, Odey; Karume, Ibrahim; Vieille, Claire; Takahashi, Masateru; Hamdan, Samir M.; European Journal of Organic Chemistry; vol. 2018; nb. 6; (2018); p. 798 - 805 View in Reaxys

HO

HO O

H O

HO

O

O

O

H

O

H

O

Rx-ID: 28201976 View in Reaxys 3/90 Yield

Conditions & References With 2-phenyl-3,4-dihydro-2H-benzo[4,5]thiazolo[3,2-a]pyrimidine, N-ethyl-N,N-diisopropylamine in tert-Amyl alcohol, toluene, Time= 10h, T= -40 °C , optical yield given as percent ee Birman, Vladimir B.; Li, Ximin; Organic Letters; vol. 10; nb. 6; (2008); p. 1115 - 1118 View in Reaxys With (S)-(–)-2-phenyl-2,3-dihydrobenzo[d]imidazo[2,1-b]thiazole, sodium sulfate, N-ethyl-N,N-diisopropylamine in chloroform, Time= 8h, T= 0 °C , Resolution of racemate, Kinetics, Reagent/catalyst, optical yield given as percent ee, enantioselective reaction

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Li, Ximin; Jiang, Hui; Uffman, Eric W.; Guo, Lei; Zhang, Yuhua; Yang, Xing; Birman, Vladimir B.; Journal of Organic Chemistry; vol. 77; nb. 4; (2012); p. 1722 - 1737 View in Reaxys With N-ethyl-N,N-diisopropylamine in chloroform, Time= 16h, T= 20 °C , enantioselective reaction Neyyappadath, Rifahath Mon; Chisholm, Ross; Greenhalgh, Mark D.; Rodríguez-Escrich, Carles; Pericàs, Miquel A.; Hähner, Georg; Smith, Andrew D.; ACS Catalysis; vol. 8; nb. 2; (2018); p. 1067 - 1075 View in Reaxys

H

H

HO

I

HO

HO H

H

H

Rx-ID: 47459570 View in Reaxys 4/90 Yield

Conditions & References Stage 1: With Me-DUPHOS, potassium methanolate, bis(pinacol)diborane, copper(l) chloride in tetrahydrofuran, Time= 12h, T= 25 °C , Glovebox Stage 2: With sodium perborate tetrahydrate in tetrahydrofuran, water, Time= 6h, T= 0 - 25 °C , Glovebox, Reagent/catalyst, enantioselective reaction Chen, Bin; Cao, Peng; Liao, Yang; Wang, Min; Liao, Jian; Organic Letters; vol. 20; nb. 5; (2018); p. 1346 - 1349 View in Reaxys

H

HO

HO

I

H

H

Rx-ID: 47459571 View in Reaxys 5/90 Yield 70 %

Conditions & References Stage 1: With (–)-(R,R)-2,3-bis(tert-butyl(methyl)phosphino)quinoxaline, potassium methanolate, bis(pinacol)diborane, copper(l) chloride in tetrahydrofuran, Time= 12h, T= 25 °C , Glovebox Stage 2: With sodium perborate tetrahydrate in tetrahydrofuran, water, Time= 6h, T= 0 - 25 °C , Glovebox, Solvent, enantioselective reaction Chen, Bin; Cao, Peng; Liao, Yang; Wang, Min; Liao, Jian; Organic Letters; vol. 20; nb. 5; (2018); p. 1346 - 1349 View in Reaxys

HO

HO

HO

H

H

Rx-ID: 8618016 View in Reaxys 6/90 Yield

Conditions & References With vinyl acetate, subtilisin in di-isopropyl ether, T= 10 - 40 °C , resolution, Thermodynamic data Ema, Tadashi; Yamaguchi, Kunihiro; Wakasa, Yuji; Tanaka, Nobuaki; Utaka, Masanori; Sakai, Takashi; Chemistry Letters; nb. 7; (2000); p. 782 - 783 View in Reaxys With MCCD-HPS packed column in hydrogenchloride, acetonitrile, pH= 8.6 Gong, Yinhan; Lee, Hian Kee; Analytical Chemistry; vol. 75; nb. 6; (2003); p. 1348 - 1354 View in Reaxys General procedure: Gas chromatographicmeasurements were performed on a GC-14B (Shimadzu, Japan) system withflame ionization detector. Nitrogen (99.999percent) was used as the carrier gas. Aη-DEX 225 capillary column (30 m long × 0.25 mm i.d. ×

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0.25 μm filmthickness, Supelco Inc.), a Chirasil L-Val capillary column (25 m long × 0.25mm i.d. × 0.12 μm film thickness, Agilent Technologies), and a Cyclosil-Bcapillary column (30 m long × 0.32 mm i.d. × 0.25 μm film thickness, AgilentTechnologies) were employed as commercial columns for comparison.

With [Co2((S)-mandelate)2(4,4'-bipyridine)3](NO3)2 coated capillary column, Time= 0.0283333h, T= 150 °C , Resolution of racemate, Reagent/catalyst Zhang, Shi-Yuan; Yang, Cheng-Xiong; Shi, Wei; Yan, Xiu-Ping; Cheng, Peng; Wojtas, Lukasz; Zaworotko, Michael J.; Chem; vol. 3; nb. 2; (2017); p. 281 - 289 View in Reaxys With Chiralpak ID in hexane, isopropyl alcohol, Resolution of racemate Ahmed, Marwa; Gwairgi, Marina; Ghanem, Ashraf; Chirality; vol. 26; nb. 11; (2014); p. 677 - 682 View in Reaxys

O

O

HO

O

HO

HO

O

H

H

H

Rx-ID: 33198467 View in Reaxys 7/90 Yield

Conditions & References With lipase AK from Pseudomonas fluorescens in tetrahydrofuran, hexane, Time= 4h, T= 30 °C , Sealed tube, optical yield given as percent ee Weiser, Diana; Boros, Zoltan; Hornyanszky, Gabor; Toth, Alexandra; Poppe, Laszlo; Process Biochemistry; vol. 47; nb. 3; (2012); p. 428 - 434 View in Reaxys With Candida antarctica lipase B in toluene, Time= 18h, T= 30 °C , Resolution of racemate, Enzymatic reaction, Kinetics, Catalytic behavior, Concentration, Solvent, enantioselective reaction Kitamoto, Yuichi; Kuruma, Yosuke; Suzuki, Kazumi; Hattori, Tetsutaro; Journal of Organic Chemistry; vol. 80; nb. 1; (2015); p. 521 - 527 View in Reaxys 4.5 General procedure for enzymatic reaction in CO2-expanded liquids General procedure: Novozym 435, bio-based liquid, alcohol, vinyl acetate, and a magnetic bar were added and sealed in a highpressure-resistant stainless-steel vessel (10mL volume) at 20°C. CO2 gas was sent into the vessel by a CO2 pump until desired pressure was achieved. The reaction mixture was magnetically stirred. At the end of the reaction, the vessel was gradually depressurized on ice. An aliquot (20μL) was filtered through EXtrelut® and diluted with diethyl ether before being analyzed by GC or HPLC. With carbon dioxide in 2-methyltetrahydrofuran, Time= 5h, T= 20 °C , p= 45004.5Torr , Sealed tube, Resolution of racemate, Enzymatic reaction, enantioselective reaction Hoang, Hai Nam; Nagashima, Yoshihiro; Mori, Shuichi; Kagechika, Hiroyuki; Matsuda, Tomoko; Tetrahedron; vol. 73; nb. 20; (2017); p. 2984 - 2989 View in Reaxys

HO

HO

H

Rx-ID: 1983183 View in Reaxys 8/90

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Yield

Conditions & References Burgess, Kevin; Jennings, Lee D.; Journal of the American Chemical Society; vol. 113; nb. 16; (1991); p. 6129 - 6139 View in Reaxys Gutman, Arie L.; Brenner, Dov; Boltanski, Aviv; Tetrahedron: Asymmetry; vol. 4; nb. 5; (1993); p. 839 - 844 View in Reaxys Suginaka, Kaoru; Hayashi, Yoshiyuki; Yamamoto, Yukio; Tetrahedron Asymmetry; vol. 7; nb. 4; (1996); p. 1153 - 1158 View in Reaxys Nakamura, Kaoru; Kawasaki, Masashi; Ohno, Atsuyoshi; Bulletin of the Chemical Society of Japan; vol. 69; nb. 4; (1996); p. 1079 - 1085 View in Reaxys Ruppert, Stephan; Gais, Hans-Joachim; Tetrahedron Asymmetry; vol. 8; nb. 21; (1997); p. 3657 - 3664 View in Reaxys Stage 1: With Candida antarctica lipase B, vinyl acetate in toluene, T= 20 °C Stage 2: With dmap, polymer-bound benzoyl chloride, triethylamine in dichloromethane, T= 20 °C Stage 3: With potassium hydroxide in tetrahydrofuran, methanol, Time= 12h, Further stages.

Cordova; Tremblay; Clapham; Janda; Journal of Organic Chemistry; vol. 66; nb. 16; (2001); p. 5645 - 5648 View in Reaxys Reaction Steps: 2 1: 44 percent Chromat. / Geotrichum candidum IFO 4597 cells on BL-100 polymer; cyclohexanone / hexane / 24 h / 30 °C 2: 65 percent / Geotrichum candidum IFO 4597 cells on BL-100 polymer; hexan-2-ol / hexane / 24 h / 30 °C With n-hexan-2-ol, Geotrichum candidum IFO 4597 cells on BL-100 polymer, cyclohexanone in hexane, 1: Oxidation / 2: Reduction Nakamura, Kaoru; Inoue, Yuko; Matsuda, Tomoko; Misawa, Ibuki; Journal of the Chemical Society - Perkin Transactions 1; nb. 16; (1999); p. 2397 - 2402 View in Reaxys Reaction Steps: 2 1: triethylamine sulfur trioxide 2: His-tagged Pseudomonas sp. metallo-η-lactamase-type alkylsulfatase Pisa1; water; tris hydrochloride / 6 h / 30 °C / pH 8.2 / Resolution of racemate; Enzymatic reaction With His-tagged Pseudomonas sp. metallo-η-lactamase-type alkylsulfatase Pisa1, water, tris hydrochloride, triethylamine sulfur trioxide Schober, Markus; Gadler, Petra; Knaus, Tanja; Kayer, Heidemarie; Birner-Gruenberger, Ruth; Guelly, Christian; MacHeroux, Peter; Wagner, Ulrike; Faber, Kurt; Organic Letters; vol. 13; nb. 16; (2011); p. 4296 - 4299 View in Reaxys Reaction Steps: 3 1: dmap / dichloromethane / 20 °C / Inert atmosphere 2: lipase from candida antartica / aq. phosphate buffer / 48 h / 30 °C 3: sodium hydroxide; water / 2 h / 20 °C With dmap, lipase from candida antartica, water, sodium hydroxide in aq. phosphate buffer, dichloromethane Kataoka, Noriyuki; Okudomi, Masayuki; Chihara, Naoka; Matsumoto, Kazutsugu; Letters in Organic Chemistry; vol. 9; nb. 9; (2012); p. 615 - 621 View in Reaxys Reaction Steps: 3 1: dmap / dichloromethane / 20 °C / Inert atmosphere 2: lipase from candida antartica / aq. phosphate buffer / 48 h / 30 °C 3: sodium hydroxide; water / 2 h / 20 °C With dmap, lipase from candida antartica, water, sodium hydroxide in aq. phosphate buffer, dichloromethane Kataoka, Noriyuki; Okudomi, Masayuki; Chihara, Naoka; Matsumoto, Kazutsugu; Letters in Organic Chemistry; vol. 9; nb. 9; (2012); p. 615 - 621 View in Reaxys Reaction Steps: 4 1: Candida antarctica lipase B / toluene / 20 °C / Enzymatic reaction

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2: potassium hydoxide; water / methanol 3: secondary alcohol dehydrogenase from Thermoanaerobacter ethanolicus W110I mutant; nicotinamide adenine dinucleotide phosphate / aq. buffer / 50 °C / pH 8.9 / Enzymatic reaction 4: secondary alcohol dehydrogenase from Thermoanaerobacter ethanolicus W110I mutant; nicotinamide adenine dinucleotide phosphate / isopropyl alcohol / 6 h / 50 °C / pH 8 / Enzymatic reaction With Candida antarctica lipase B, secondary alcohol dehydrogenase from Thermoanaerobacter ethanolicus W110I mutant, water, nicotinamide adenine dinucleotide phosphate, potassium hydoxide in methanol, isopropyl alcohol, toluene Patel, Jay M.; Musa, Musa M.; Rodriguez, Luis; Sutton, Dewey A.; Popik, Vladimir V.; Phillips, Robert S.; Organic and Biomolecular Chemistry; vol. 12; nb. 31; (2014); p. 5905 - 5910 View in Reaxys Reaction Steps: 4 1: Candida antarctica lipase B / toluene / 20 °C / Enzymatic reaction 2: potassium hydoxide; water / methanol 3: secondary alcohol dehydrogenase from Thermoanaerobacter ethanolicus W110I mutant; nicotinamide adenine dinucleotide phosphate / aq. buffer / 50 °C / pH 8.9 / Enzymatic reaction 4: nicotinamide adenine dinucleotide phosphate; secondary alcohol dehydrogenase from Thermoanaerobacter ethanolicus W110A mutant / isopropyl alcohol / 6 h / 50 °C / pH 8 / Enzymatic reaction With Candida antarctica lipase B, secondary alcohol dehydrogenase from Thermoanaerobacter ethanolicus W110A mutant, secondary alcohol dehydrogenase from Thermoanaerobacter ethanolicus W110I mutant, water, nicotinamide adenine dinucleotide phosphate, potassium hydoxide in methanol, isopropyl alcohol, toluene Patel, Jay M.; Musa, Musa M.; Rodriguez, Luis; Sutton, Dewey A.; Popik, Vladimir V.; Phillips, Robert S.; Organic and Biomolecular Chemistry; vol. 12; nb. 31; (2014); p. 5905 - 5910 View in Reaxys Reaction Steps: 2 1: Thermoanaerobacter ethanolicus secondary alcohol dehydrogenase W110G mutant; NADP / acetone / 24 h / 50 °C / pH 8 / Enzymatic reaction 2: Thermoanaerobacter ethanolicus secondary alcohol dehydrogenase W110G mutant; NADP / acetone; isopropyl alcohol / 24 h / 50 °C / pH 8 / Enzymatic reaction With Thermoanaerobacter ethanolicus secondary alcohol dehydrogenase W110G mutant, NADP in isopropyl alcohol, acetone Karume, Ibrahim; Takahashi, Masateru; Hamdan, Samir M.; Musa, Musa M.; ChemCatChem; vol. 8; nb. 8; (2016); p.

1459 - 1463 View in Reaxys

HO

HO

O

HO

H

H

Rx-ID: 5195147 View in Reaxys 9/90 Yield 66 %

Conditions & References With (1R)-N-oxyl-1-(N-benzylcarbamoyl)-8-azabicyclo[3.2.1]octane, sodium hydrogencarbonate, sodium bromide in dichloromethane, water, T= 0 °C , Electrochemical reaction, optical yield given as percent ee, enantioselective reaction Demizu, Yosuke; Shiigi, Hirofumi; Mori, Hiroyuki; Matsumoto, Kazuya; Onomura, Osamu; Tetrahedron Asymmetry; vol.

19; nb. 23; (2008); p. 2659 - 2665 View in Reaxys

40 %

With Sphingomonas paucimobilis NCIMB 8195 in water, N,N-dimethyl-formamide, Time= 120h Allan; Carnell; Journal of Organic Chemistry; vol. 66; nb. 19; (2001); p. 6495 - 6497 View in Reaxys

44 % Chromat.

With Geotrichum candidum IFO 4597 cells on BL-100 polymer, cyclohexanone in hexane, Time= 24h, T= 30 °C , Oxidation Nakamura, Kaoru; Inoue, Yuko; Matsuda, Tomoko; Misawa, Ibuki; Journal of the Chemical Society - Perkin Transactions 1; nb. 16; (1999); p. 2397 - 2402 View in Reaxys

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Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

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50.9 % Chromat.

With air, (R,R)-(nitroso)(salen)ruthenium(II) chloride in toluene, Time= 17h, T= 20 °C , Irradiation, resolution of racemate; oxidation Masutani, Kouta; Uchida, Tatsuya; Irie, Ryo; Katsuki, Tsutomu; Tetrahedron Letters; vol. 41; nb. 26; (2000); p. 5119 - 5123 View in Reaxys With [bis(acetoxy)iodo]benzene, tetraethylammonium bromide, [Mn{CHPhNCH[OC6H2(t-Bu)2]}2]PF6 in water, Time= 0.5h, T= 20 °C , Product distribution, Further Variations: Catalysts, reaction times Sun, Wei; Wang, Hongwang; Xia, Chungu; Li, Jingwei; Zhao, Peiqing; Angewandte Chemie - International Edition; vol. 42; nb. 9; (2003); p. 1042 - 1044 View in Reaxys With lyophilized cells of Rhodococcus ruber DSM 44541, acetone in phosphate buffer, Time= 24h, T= 24 °C , pH= 8.0, Title compound not separated from byproducts Stampfer, Wolfgang; Kosjek, Birgit; Faber, Kurt; Kroutil, Wolfgang; Journal of Organic Chemistry; vol. 68; nb. 2; (2003); p. 402 - 406 View in Reaxys With air, chiral Ru(salen)(nitrosyl) complex in chloroform, Time= 11h, T= 20 °C , UV-irradiation, Kinetics Nakamura, Yukie; Egami, Hiromichi; Matsumoto, Kazuhiro; Uchida, Tatsuya; Katsuki, Tsutomu; Tetrahedron; vol. 63; nb. 28; (2007); p. 6383 - 6387 View in Reaxys With air, chiral Ru(salen)(nitrosyl) complex in chloroform, T= 20 °C , UV-irradiation, Title compound not separated from byproducts.

Nakamura, Yukie; Egami, Hiromichi; Matsumoto, Kazuhiro; Uchida, Tatsuya; Katsuki, Tsutomu; Tetrahedron; vol. 63; nb. 28; (2007); p. 6383 - 6387 View in Reaxys With Thermoanaerobacter ethanolicus secondary alcohol dehydrogenase W110G mutant, NADP in acetone, Time= 24h, T= 50 °C , pH= 8, Enzymatic reaction, Reagent/catalyst, enantioselective reaction Karume, Ibrahim; Takahashi, Masateru; Hamdan, Samir M.; Musa, Musa M.; ChemCatChem; vol. 8; nb. 8; (2016); p.

1459 - 1463 View in Reaxys

O

O

HO

O

HO

O O

H

O

H

H

Rx-ID: 9301814 View in Reaxys 10/90 Yield

Conditions & References With lipase from Pseudomonas cepacia immobilized on ceramic in toluene, Time= 4h, T= 40 °C Ghanem, Ashraf; Schurig, Volker; Monatshefte fur Chemie; vol. 134; nb. 8; (2003); p. 1151 - 1157 View in Reaxys With Candida antarctica lipase B in hexane, Time= 3h, T= 50 °C , Resolution of racemate, Time, enantioselective reaction Karume, Ibrahim; Musa, Musa M.; Bsharat, Odey; Takahashi, Masateru; Hamdan, Samir M.; El Ali, Bassam; RSC Advances; vol. 6; nb. 99; (2016); p. 96616 - 96622 View in Reaxys

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HO

HO

O

O

H

O

O

Rx-ID: 10286953 View in Reaxys 11/90 Yield

Conditions & References With Burkholderia cepacia lipase immobilized on ceramic particles in hexane, Time= 48h, T= 20 °C Kiss, Violetta; Egri, Gabriella; Balint, Jozsef; Ling, Istvan; Barkoczi, Jozsef; Fogassy, Elemer; Tetrahedron Asymmetry; vol. 17; nb. 15; (2006); p. 2220 - 2234 View in Reaxys Enantioselectivity of PHL for Transesterication of Sec-Alcohols.

General procedure: Enantioselectivity of PHL for Transesterication of Sec-Alcohols. The reaction mixture was prepared by mixing arac-alcohol (3a–h, 0.1 mmol), vinyl butyrate (39 μL,0.3 mmol), and immobilized PHL (20 mg) in t-butylmethyl ether (MTBE, 1 mL). The reaction mixture wasshaken at 200 rpm. A little amount of the reaction mixture(200 μL) was retrieved and dissolved in MTBE (1 mL).After centrifugation of the diluted reaction mixture toremove the immobilized PHL, the clear solution was ana-lyzed by a GC (Agilent 6890N; Agilent Technologies,Seoul, Korea) equipped with a chiral capillary column(Cyclosil-B 30 m 0.25 mm). The GC analysis conditionfor the reaction with 3e: initial column temperature 80Cfor 5 min, ramp up to 120C at a rate of 2.5C/min, andthen held at 120C for 15 min.

With lipase from Pseudozyma hubeiensis SY62 in tert-butyl methyl ether, Time= 44h, T= 25 °C , enantioselective reaction Park, Seongsoon; Bulletin of the Korean Chemical Society; vol. 37; nb. 10; (2016); p. 1720 - 1723 View in Reaxys

HO

HO

Li H

H

O

Rx-ID: 33825505 View in Reaxys 12/90 Yield

Conditions & References

80 %

With triisopropoxytitanium(IV) chloride, (Sa)-2'-((S)-hydroxy(phenyl)methyl)-[1,1'-binaphthalen]-2-ol in diethyl ether, hexane, Time= 0.166667h, T= -20 °C , enantioselective reaction Veguillas, Marcos; Solà, Ricard; Shaw, Luke; Maciá, Beatriz; European Journal of Organic Chemistry; vol. 2016; nb. 9; (2016); p. 1788 - 1794 View in Reaxys Stage 1: With (Sa)-2'-[(R)-hydroxy(phenyl)methyl]-(1,1'-binaphthalen)-2-ol, titanium(IV)isopropoxide in toluene, Time= 1h, T= -40 °C , Inert atmosphere Stage 2: With hydrogenchloride in water, Inert atmosphere, optical yield given as percent ee, enantioselective reaction Fernandez-Mateos, Emilio; MacIa, Beatriz; Yus, Miguel; European Journal of Organic Chemistry; nb. 20; (2012); p. 3732 3736 View in Reaxys

HO

HO

H

H

Rx-ID: 35211918 View in Reaxys 13/90 Yield

Conditions & References With Thermoanaerobacter ethanolicus secondary alcohol dehydrogenase W110A, NAD, NADPH in N,N-dimethyl-formamide, Time= 48h, T= 50 °C , pH= 8, Enzymatic reaction, Solvent Musa, Musa M.; Phillips, Robert S.; Laivenieks, Maris; Vieille, Claire; Takahashi, Masateru; Hamdan, Samir M.; Organic and Biomolecular Chemistry; vol. 11; nb. 17; (2013); p. 2911 - 2915

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View in Reaxys Reaction Steps: 2 1: secondary alcohol dehydrogenase from Thermoanaerobacter ethanolicus W110I mutant; nicotinamide adenine dinucleotide phosphate / aq. buffer / 50 °C / pH 8.9 / Enzymatic reaction 2: secondary alcohol dehydrogenase from Thermoanaerobacter ethanolicus W110I mutant; nicotinamide adenine dinucleotide phosphate / isopropyl alcohol / 6 h / 50 °C / pH 8 / Enzymatic reaction With secondary alcohol dehydrogenase from Thermoanaerobacter ethanolicus W110I mutant, nicotinamide adenine dinucleotide phosphate in isopropyl alcohol Patel, Jay M.; Musa, Musa M.; Rodriguez, Luis; Sutton, Dewey A.; Popik, Vladimir V.; Phillips, Robert S.; Organic and Biomolecular Chemistry; vol. 12; nb. 31; (2014); p. 5905 - 5910 View in Reaxys Reaction Steps: 2 1: secondary alcohol dehydrogenase from Thermoanaerobacter ethanolicus W110I mutant; nicotinamide adenine dinucleotide phosphate / aq. buffer / 50 °C / pH 8.9 / Enzymatic reaction 2: nicotinamide adenine dinucleotide phosphate; secondary alcohol dehydrogenase from Thermoanaerobacter ethanolicus W110A mutant / isopropyl alcohol / 6 h / 50 °C / pH 8 / Enzymatic reaction With secondary alcohol dehydrogenase from Thermoanaerobacter ethanolicus W110A mutant, secondary alcohol dehydrogenase from Thermoanaerobacter ethanolicus W110I mutant, nicotinamide adenine dinucleotide phosphate in isopropyl alcohol Patel, Jay M.; Musa, Musa M.; Rodriguez, Luis; Sutton, Dewey A.; Popik, Vladimir V.; Phillips, Robert S.; Organic and Biomolecular Chemistry; vol. 12; nb. 31; (2014); p. 5905 - 5910 View in Reaxys With Thermoanaerobacter ethanolicus secondary alcohol dehydrogenase W110A mutant, nicotinamide adenine dinucleotide phosphate, NADPH in hexane, Time= 24h, T= 50 °C Karume, Ibrahim; Musa, Musa M.; Bsharat, Odey; Takahashi, Masateru; Hamdan, Samir M.; El Ali, Bassam; RSC Advances; vol. 6; nb. 99; (2016); p. 96616 - 96622 View in Reaxys

O HO

Ti

HO

(v4)

O

O H

H

O

Rx-ID: 42849729 View in Reaxys 14/90 Yield

Conditions & References 11 : 4.2. General procedure for the addition of methyltriisopropoxititanium to aldehydes-general procedure A General procedure: To a stirred solution of L1 or L2 (0.2 equiv) in Et2O (3.0mL, 0.067M) at 0°C, MeTi(OiPr)3 (0.3mL, 1.5equiv, 1M in THF, unless stated otherwise) was added. The solution was stirred for 1 min and then the aldehyde (0.1 mmol) was added.

The reaction was stirred for 90 min and then quenched with water. The layers were separated and the aqueous layer was extracted three times with Et2O. The combined organic layers were dried over anhydrous MgSO4 and the solvent was removed under reduced pressure. The reaction crude was purified by flash silica gel chromatography. 4.2.11 (R)-1-Phenylpropan-2-ol 2k 21

Following general procedure A, the reaction of phenylacetaldehyde (12 μL, 0.1 mmol) with methyltriisopropoxytitanium (0.15 mL, 1.5 equiv, 1.0 M in THF) in the presence of (Ra,S)-Py-BINMOL L2 (3.8 mg, 0.1 equiv) in Et2O (1.5 mL) provided (R)-1phenylpropan-2-ol (13 mg) as a colorless oil after column chromatography (Hex/EtOAc 9:1). Yield: 93percent. Ee: 85percent. [η]D 25 = -35.4 (c 0.7, CHCl3) {Lit. 21

[η]D 28 = -35.4 (c 0.8, CHCl3) for 99percent ee}.

Ee determination by chiral GC analysis, Cyclosil η column, T = 85 °C, P = 15.9 psi, retention times: tr(S) = 76.0 min, tr(R) = 78.2 min (major enantiomer).

With (Ra)-2'-[(S)-hydroxy(pyridin-4-yl)methyl]-(1,1'-binaphthalen)-2-ol in tetrahydrofuran, diethyl ether, Time= 1h, T= 0 °C , Reagent/catalyst, Overall yield = 93 percent; Overall yield = 13 mg; enantioselective reaction

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Veguillas, Marcos; Solà, Ricard; Fernández-Ibañez, M. Ángeles; Maciá, Beatriz; Tetrahedron Asymmetry; vol. 27; nb.

14-15; (2016); p. 643 - 648 View in Reaxys F

F

HO

O F

O

HO

O

O H

O

O

H

Rx-ID: 43934109 View in Reaxys 15/90 Yield

Conditions & References With Candida antarctica lipase B in hexane, Time= 3h, T= 50 °C , Resolution of racemate, enantioselective reaction Karume, Ibrahim; Musa, Musa M.; Bsharat, Odey; Takahashi, Masateru; Hamdan, Samir M.; El Ali, Bassam; RSC Advances; vol. 6; nb. 99; (2016); p. 96616 - 96622 View in Reaxys

O

HO

O

O

HO

O O

H

O

H

H

Rx-ID: 43934160 View in Reaxys 16/90 Yield

Conditions & References With Candida antarctica lipase B in hexane, Time= 3h, T= 50 °C , Resolution of racemate, enantioselective reaction Karume, Ibrahim; Musa, Musa M.; Bsharat, Odey; Takahashi, Masateru; Hamdan, Samir M.; El Ali, Bassam; RSC Advances; vol. 6; nb. 99; (2016); p. 96616 - 96622 View in Reaxys

HO

HO

O

H

H

O

Rx-ID: 44024819 View in Reaxys 17/90 Yield

Conditions & References With water, sodium hydroxide in methanol, Time= 6h Cozett, Rudy E.; Venter, Gerhard A.; Gokada, Maheswara Rao; Hunter, Roger; Organic and Biomolecular Chemistry; vol.

14; nb. 46; (2016); p. 10914 - 10925 View in Reaxys

O

O

HO

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O

HO

H

O

HO

O

O

H

H

H

Rx-ID: 26054982 View in Reaxys 18/90 Yield

Conditions & References With Candida antarctica lipase B immobilized on acrylic resin in tetrahydrofuran, hexane, T= 25 °C , p= 750.075Torr , Title compound not separated from byproducts.

Csajagi, Csaba; Szatzker, Gabor; Rita Toke, Eniko; Uerge, Laszlo; Darvas, Ferenc; Poppe, Laszlo; Tetrahedron Asymmetry; vol. 19; nb. 2; (2008); p. 237 - 246 View in Reaxys With Candida antarctica lipase B in acetonitrile, Time= 18h, T= 30 °C , Resolution of racemate, Enzymatic reaction, stereoselective reaction Kitamoto, Yuichi; Kuruma, Yosuke; Suzuki, Kazumi; Hattori, Tetsutaro; Journal of Organic Chemistry; vol. 80; nb. 1; (2015); p. 521 - 527 View in Reaxys

O

Br

HO

HO

H

H

H

H

HO

HO

Rx-ID: 39553818 View in Reaxys 19/90 Yield

Conditions & References

11 %, 3 %

With [2,2]bipyridinyl, manganese, (1,2-dimethoxyethane)dichloronickel(II), bis(.eta.5((1R,2S,5R)-5-methyl-2-[prop-2-yl]-cyclohex-1-yl)cyclopentadienyl)-titanium dichloride, triethylamine hydrochloride in benzene, Time= 12h, T= 20 °C , Inert atmosphere, Glovebox, Autoclave, enantioselective reaction Zhao, Yang; Weix, Daniel J.; Journal of the American Chemical Society; vol. 137; nb. 9; (2015); p. 3327 - 3340 View in Reaxys

HO

O

HO

B

H

O

H

Rx-ID: 41497327 View in Reaxys 20/90 Yield

Conditions & References With sodium perborate tetrahydrate in tetrahydrofuran, water, Inert atmosphere, Schlenk technique Borràs, Carlota; Biosca, Maria; Pàmies, Oscar; Diéguez, Montserrat; Organometallics; vol. 34; nb. 21; (2015); p. 5321 5334 View in Reaxys

O

O

HO

O

HO

O

H

H

Rx-ID: 9512159 View in Reaxys 21/90

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Yield

Conditions & References With Pseudomonas cepacia lipase, 4 A molecular sieve, peracetylated η-cyclodextrin in toluene, Time= 2h, T= 40 °C , Title compound not separated from byproducts Ghanem, Ashraf; Schurig, Volker; Tetrahedron Asymmetry; vol. 14; nb. 17; (2003); p. 2547 - 2555 View in Reaxys With Candida antarctica lipase B in toluene, T= 20 °C , Enzymatic reaction Patel, Jay M.; Musa, Musa M.; Rodriguez, Luis; Sutton, Dewey A.; Popik, Vladimir V.; Phillips, Robert S.; Organic and Biomolecular Chemistry; vol. 12; nb. 31; (2014); p. 5905 - 5910 View in Reaxys

HO

H

Rx-ID: 37560875 View in Reaxys 22/90 Yield

Conditions & References With D-Glucose in aq. phosphate buffer, dimethyl sulfoxide, Time= 4h, T= 30 °C , pH= 8, enantioselective reaction Yang, Yi; Liu, Ji; Li, Zhi; Angewandte Chemie - International Edition; vol. 53; nb. 12; (2014); p. 3120 - 3124; Angew. Chem.; vol. 126; nb. 12; (2014); p. 3348,1 View in Reaxys

HO

HO

H

H

Rx-ID: 37560876 View in Reaxys 23/90 Yield

Conditions & References With D-Glucose in aq. phosphate buffer, dimethyl sulfoxide, Time= 4h, T= 30 °C , pH= 8, enantioselective reaction Yang, Yi; Liu, Ji; Li, Zhi; Angewandte Chemie - International Edition; vol. 53; nb. 12; (2014); p. 3120 - 3124; Angew. Chem.; vol. 126; nb. 12; (2014); p. 3348,1 View in Reaxys

HO

HO

HO H

H

Rx-ID: 37560878 View in Reaxys 24/90 Yield

Conditions & References With D-Glucose in aq. phosphate buffer, dimethyl sulfoxide, Time= 4h, T= 30 °C , pH= 8, Reagent/catalyst, enantioselective reaction Yang, Yi; Liu, Ji; Li, Zhi; Angewandte Chemie - International Edition; vol. 53; nb. 12; (2014); p. 3120 - 3124; Angew. Chem.; vol. 126; nb. 12; (2014); p. 3348,1 View in Reaxys

HO O

O

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HO

HO

O H

H

O H

Rx-ID: 37926123 View in Reaxys 25/90 Yield

Conditions & References 2.6 General procedure for LH-EP immobilized SmL catalyzed resolution of racemic alcohols General procedure: A certain molar ratios of racemic alcohol and acyl donor such as vinyl butyrate in an organic solvent (5mL) was mixed with appropriate amount of immobilized lipase in a 25mL screw capped vial in a thermostatted shaker. The reaction was monitored and the ee assessed by HPLC analysis on the chiral columns as stated in the HPLC Analysis section. Aliquots (50μL) of the reaction mixture were withdrawn at intervals, diluted with n-hexane/2-propanol (9:1, 450μL), centrifuged and the supernatant (10μL) was then injected onto the column.

With LH-EP immobilized Serratia marcescens H30 lipase in hexane, Time= 36h, T= 45 °C , Resolution of racemate, enantioselective reaction Su, Erzheng; Xu, Jingjing; You, Pengyong; Journal of Molecular Catalysis B: Enzymatic; vol. 106; (2014); p. 11 - 16 View in Reaxys

O

HO

O

H

H

Rx-ID: 38389794 View in Reaxys 26/90 Yield

Conditions & References Reaction Steps: 3 1: potassium hydoxide; water / methanol 2: secondary alcohol dehydrogenase from Thermoanaerobacter ethanolicus W110I mutant; nicotinamide adenine dinucleotide phosphate / aq. buffer / 50 °C / pH 8.9 / Enzymatic reaction 3: secondary alcohol dehydrogenase from Thermoanaerobacter ethanolicus W110I mutant; nicotinamide adenine dinucleotide phosphate / isopropyl alcohol / 6 h / 50 °C / pH 8 / Enzymatic reaction With secondary alcohol dehydrogenase from Thermoanaerobacter ethanolicus W110I mutant, water, nicotinamide adenine dinucleotide phosphate, potassium hydoxide in methanol, isopropyl alcohol Patel, Jay M.; Musa, Musa M.; Rodriguez, Luis; Sutton, Dewey A.; Popik, Vladimir V.; Phillips, Robert S.; Organic and Biomolecular Chemistry; vol. 12; nb. 31; (2014); p. 5905 - 5910 View in Reaxys Reaction Steps: 3 1: potassium hydoxide; water / methanol 2: secondary alcohol dehydrogenase from Thermoanaerobacter ethanolicus W110I mutant; nicotinamide adenine dinucleotide phosphate / aq. buffer / 50 °C / pH 8.9 / Enzymatic reaction 3: nicotinamide adenine dinucleotide phosphate; secondary alcohol dehydrogenase from Thermoanaerobacter ethanolicus W110A mutant / isopropyl alcohol / 6 h / 50 °C / pH 8 / Enzymatic reaction With secondary alcohol dehydrogenase from Thermoanaerobacter ethanolicus W110A mutant, secondary alcohol dehydrogenase from Thermoanaerobacter ethanolicus W110I mutant, water, nicotinamide adenine dinucleotide phosphate, potassium hydoxide in methanol, isopropyl alcohol Patel, Jay M.; Musa, Musa M.; Rodriguez, Luis; Sutton, Dewey A.; Popik, Vladimir V.; Phillips, Robert S.; Organic and Biomolecular Chemistry; vol. 12; nb. 31; (2014); p. 5905 - 5910 View in Reaxys

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HO

HO

H HO

H

H

Rx-ID: 39376770 View in Reaxys 27/90 Yield

Conditions & References With D-glucose, GDH, cytochrome P450 monooxygenase CYP116B4 from Labrenzia aggregata, nicotinamide adenine dinucleotide phosphate in aq. buffer, Time= 5h, T= 30 °C , pH= 8.5, Enzymatic reaction, enantioselective reaction Yin, Yue-Cai; Yu, Hui-Lei; Luan, Zheng-Jiao; Li, Ren-Jie; Ouyang, Peng-Fei; Liu, Jing; Xu, Jian-He; ChemBioChem; vol. 15; nb. 16; (2014); p. 2443 - 2449 View in Reaxys With nicotinamide adenine dinucleotide phosphate, cytochrome P450 monooxygenase from Labrenzia aggregata in aq. buffer, Time= 5h, T= 30 °C , pH= 8.5, Enzymatic reaction, enantioselective reaction Yin, Yue-Cai; Yu, Hui-Lei; Luan, Zheng-Jiao; Li, Ren-Jie; Ouyang, Peng-Fei; Liu, Jing; Xu, Jian-He; ChemBioChem; vol. 15; nb. 16; (2014); p. 2443 - 2449 View in Reaxys

HO O

Br

H

Rx-ID: 10232451 View in Reaxys 28/90 Yield

Conditions & References Stage 1: With magnesium in tetrahydrofuran, Time= 1h, T= 0 °C , Inert atmosphere Stage 2: With copper(l) cyanide in tetrahydrofuran, Time= 0.5h, T= -35 °C Stage 3: in tetrahydrofuran, Time= 1.5h, T= -35 - 20 °C Taguri, Tomonori; Yamamoto, Masanobu; Fujii, Toru; Muraki, Yuta; Ando, Tetsu; European Journal of Organic Chemistry; nb. 30; (2013); p. 6924 - 6933 View in Reaxys Stage 1: With n-butyllithium in tetrahydrofuran, hexane, Time= 0.333333h, T= -70 °C Stage 2: in tetrahydrofuran, hexane, Time= 1.83333h, T= -50 - 20 °C Erdelyi, Balazs; Szabo, Antal; Seres, Gabor; Birincsik, Laszlo; Ivanics, Jozsef; Szatzker, Gabor; Poppe, Laszlo; Tetrahedron Asymmetry; vol. 17; nb. 2; (2006); p. 268 - 274 View in Reaxys

HO O

O H

O

OH

Rx-ID: 29753835 View in Reaxys 29/90 Yield

Conditions & References Stage 1: With dmap, dicyclohexyl-carbodiimide in dichloromethane, T= 20 °C , Inert atmosphere Stage 2: With immobilized Candida antarctica Lipase B, water in hexane, Time= 24h, T= 30 °C , pH= 6.5, aq. phosphate buffer, Enzymatic reaction Stage 3: With water, sodium hydroxide in methanol, Time= 1h, T= 20 °C , optical yield given as percent ee, enantioselective reaction

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Okudomi, Masayuki; Ageishi, Kanpei; Yamada, Tomomi; Chihara, Naoka; Nakagawa, Takuya; Mizuochi, Katsumi; Matsumoto, Kazutsugu; Tetrahedron; vol. 66; nb. 40; (2010); p. 8060 - 8067 View in Reaxys Reaction Steps: 2 1: lipase from candida antartica / aq. phosphate buffer / 48 h / 30 °C 2: sodium hydroxide; water / 2 h / 20 °C With lipase from candida antartica, water, sodium hydroxide in aq. phosphate buffer Kataoka, Noriyuki; Okudomi, Masayuki; Chihara, Naoka; Matsumoto, Kazutsugu; Letters in Organic Chemistry; vol. 9; nb. 9; (2012); p. 615 - 621 View in Reaxys

HO

HO

Al H

H

O

Rx-ID: 33714582 View in Reaxys 30/90 Yield

Conditions & References 4.2. General procedure for the synthesis of chiral alcohols General procedure: In a flame dried Schlenk tube, (Sa,R)-L1 (11.4 mg, 0.03 mmol) was dissolved in anhydrous Et2O (2.5 mL) and Ti(i-PrO)4 (366 μL, 4 equiv, 1.2 mmol) was added to the solution at 0 °C. After 5 min, R3Al (1.5 equiv, 0.45 mmol) was added followed by the addition of the corresponding aldehyde (0.3 mmol). The reaction mixture was stirred at 0 °C for 1 h (in the case of Me3Al) or 3 h (for the rest of organoaluminum reagents) and then quenched with 2 mL of H2O and 2 mL of HCl 2 M. The crude product was extracted with EtOAc (3 .x. 5 mL) and the combined organic layers were neutralized with aq satd NaHCO3, dried over MgSO4, and concentrated in vacuo. The crude product was purified by distillation or chromatography on silica gel to give the desired alcohol 2, whose data were in agreement with those previously reported in the literature.6c Stage 1: With titanium(IV) isopropylate, (Sa)-2'-[(R)-hydroxy(phenyl)methyl]-(1,1'-binaphthalen)-2-ol in diethyl ether, toluene, Time= 1h, T= 0 °C , Inert atmosphere Stage 2: With hydrogenchloride in diethyl ether, water, toluene, Inert atmosphere, optical yield given as percent ee, enantioselective reaction Fernandez-Mateos, Emilio; MacIa, Beatriz; Yus, Miguel; Tetrahedron Asymmetry; vol. 23; nb. 10; (2012); p. 789 - 794 View in Reaxys

O

HO

HO

H

Rx-ID: 34106261 View in Reaxys 31/90 Yield

Conditions & References With Arthrobacter atrocyaneus in N,N-dimethyl-formamide, Time= 72h, T= 32 °C , Microbiological reaction, enantioselective reaction Silva, Camila R.; Souza, Juliana C.; Araujo, Lidiane S.; Kagohara, Edna; Garcia, Thais P.; Pelizzari, Vivian H.; Andrade, Leandro H.; Journal of Molecular Catalysis B: Enzymatic; vol. 83; (2012); p. 23 - 28 View in Reaxys O

HO O OH

H O

Rx-ID: 34605497 View in Reaxys 32/90 Yield

Conditions & References Reaction Steps: 2

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1: lipase from candida antartica / aq. phosphate buffer / 48 h / 30 °C 2: sodium hydroxide; water / 2 h / 20 °C With lipase from candida antartica, water, sodium hydroxide in aq. phosphate buffer Kataoka, Noriyuki; Okudomi, Masayuki; Chihara, Naoka; Matsumoto, Kazutsugu; Letters in Organic Chemistry; vol. 9; nb. 9; (2012); p. 615 - 621 View in Reaxys

O O

HO

HO O

H

Rx-ID: 34605513 View in Reaxys 33/90 Yield

Conditions & References With water, sodium hydroxide, Time= 2h, T= 20 °C Kataoka, Noriyuki; Okudomi, Masayuki; Chihara, Naoka; Matsumoto, Kazutsugu; Letters in Organic Chemistry; vol. 9; nb. 9; (2012); p. 615 - 621 View in Reaxys

HO

O HO

O

O H

Rx-ID: 34605514 View in Reaxys 34/90 Yield

Conditions & References With water, sodium hydroxide, Time= 2h, T= 20 °C Kataoka, Noriyuki; Okudomi, Masayuki; Chihara, Naoka; Matsumoto, Kazutsugu; Letters in Organic Chemistry; vol. 9; nb. 9; (2012); p. 615 - 621 View in Reaxys

H

HO

H

O

Rx-ID: 4997925 View in Reaxys 35/90 Yield

Conditions & References With lithium aluminium tetrahydride in tetrahydrofuran, Time= 2h, Heating Talluri, Siva Kumar; Sudalai, Arumugam; Tetrahedron; vol. 63; nb. 39; (2007); p. 9758 - 9763 View in Reaxys With lithium aluminium tetrahydride in diethyl ether, Time= 2h, Heating D'Arrigo, Paola; Fuganti, Claudio; Pedrocchi Fantoni, Giuseppe; Servi, Stefano; Tetrahedron; vol. 54; nb. 49; (1998); p.

15017 - 15026 View in Reaxys D'Arrigo, Paola; Lattanzio, Maria; Fantoni, Giuseppe Pedrocchi; Servi, Stefano; Tetrahedron Asymmetry; vol. 9; nb. 22; (1998); p. 4021 - 4026 View in Reaxys With sodium tetrahydroborate in ethanol, Time= 2h, Reflux, regioselective reaction

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Kondekar, Nagendra B.; Kumar, Pradeep; Synthetic Communications; vol. 41; nb. 9; (2011); p. 1301 - 1308 View in Reaxys

HO

O

H

Rx-ID: 30642936 View in Reaxys 36/90 Yield

Conditions & References Reaction Steps: 2 1.1: (S,S)-(salen)cobalt(III)(OAc) / 0.08 h / 0 °C 1.2: 8 h / 0 °C 2.1: sodium tetrahydroborate / ethanol / 2 h / Reflux With sodium tetrahydroborate, (S,S)-(salen)cobalt(III)(OAc) in ethanol Kondekar, Nagendra B.; Kumar, Pradeep; Synthetic Communications; vol. 41; nb. 9; (2011); p. 1301 - 1308 View in Reaxys

HO

H O

Rx-ID: 30642949 View in Reaxys 37/90 Yield

Conditions & References Reaction Steps: 3 1.1: sodium hydride / dimethyl sulfoxide / 1 h 1.2: 5 h / 25 °C 2.1: (S,S)-(salen)cobalt(III)(OAc) / 0.08 h / 0 °C 2.2: 8 h / 0 °C 3.1: sodium tetrahydroborate / ethanol / 2 h / Reflux With sodium tetrahydroborate, (S,S)-(salen)cobalt(III)(OAc), sodium hydride in ethanol, dimethyl sulfoxide Kondekar, Nagendra B.; Kumar, Pradeep; Synthetic Communications; vol. 41; nb. 9; (2011); p. 1301 - 1308 View in Reaxys

HO

O

HO

S O

O OH

O

H

S O O

Rx-ID: 31556591 View in Reaxys 38/90 Yield

Conditions & References With His-tagged Pseudomonas sp. metallo-η-lactamase-type alkylsulfatase Pisa1, water, tris hydrochloride, Time= 6h, T= 30 °C , pH= 8.2, Resolution of racemate, Enzymatic reaction, optical yield given as percent ee, stereoselective reaction Schober, Markus; Gadler, Petra; Knaus, Tanja; Kayer, Heidemarie; Birner-Gruenberger, Ruth; Guelly, Christian; MacHeroux, Peter; Wagner, Ulrike; Faber, Kurt; Organic Letters; vol. 13; nb. 16; (2011); p. 4296 - 4299 View in Reaxys

HO Mg

HO

Br

H

H

O

Rx-ID: 32115466 View in Reaxys 39/90

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Yield

Conditions & References Stage 1: With titanium(IV) isopropylate, (Sa)-2'-[(R)-hydroxy(phenyl)methyl]-(1,1'-binaphthalen)-2-ol in toluene, Time= 0.166667h, T= -20 °C , Inert atmosphere Stage 2: in toluene, Time= 4h, T= -40 °C , Inert atmosphere, Grignard reaction, optical yield given as percent ee, enantioselective reaction Fernandez-Mateos, Emilio; MacIa, Beatriz; Ramon, Diego J.; Yus, Miguel; European Journal of Organic Chemistry; nb. 34; (2011); p. 6851 - 6855 View in Reaxys O

HO

HO

O OH

H

H

O

Rx-ID: 29753833 View in Reaxys 40/90 Yield

Conditions & References Stage 1: With dmap, dicyclohexyl-carbodiimide in dichloromethane, T= 20 °C , Inert atmosphere Stage 2: With immobilized Candida antarctica Lipase B, water in hexane, Time= 24h, T= 30 °C , pH= 6.5, aq. phosphate buffer, Enzymatic reaction Stage 3: With water, sodium hydroxide in methanol, Time= 1h, T= 20 °C , optical yield given as percent ee, enantioselective reaction Okudomi, Masayuki; Ageishi, Kanpei; Yamada, Tomomi; Chihara, Naoka; Nakagawa, Takuya; Mizuochi, Katsumi; Matsumoto, Kazutsugu; Tetrahedron; vol. 66; nb. 40; (2010); p. 8060 - 8067 View in Reaxys

O

HO

HO

Cl H

O

H

Rx-ID: 29758101 View in Reaxys 41/90 Yield

Conditions & References With Pseudomonas fluorescence lipase, Resolution of racemate, Enzymatic reaction, optical yield given as percent ee Scholz, Roland; Hellmann, Gunther; Rohs, Susanne; Oezdemir, Diana; Raabe, Gerhard; Vermeeren, Cornelia; Gais, Hans-Joachim; European Journal of Organic Chemistry; nb. 24; (2010); p. 4588 - 4616 View in Reaxys

Br

HO

HO

H

Br

Br

H

H

H

Rx-ID: 29809598 View in Reaxys 42/90 Yield

Conditions & References With Sphingobium japonicum haloalkane dehalogenase, T= 21 °C , pH= 8.2, Tris sulfate buffer, Resolution of racemate, Enzymatic reaction, enantioselective reaction Prokop, Zbynek; Sato, Yukari; Brezovsky, Jan; Mozga, Tomas; Chaloupkova, Radka; Koudelakova, Tana; Jerabek, Petr; Stepankova, Veronika; Natsume, Ryo; Van Leeuwen, Jan G. E.; Janssen, Dick B.; Florian, Jan; Nagata, Yuji; Senda, Toshiya; Damborsky, Jiri; Angewandte Chemie - International Edition; vol. 49; nb. 35; (2010); p. 6111 - 6115 View in Reaxys

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26/41

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HO

HO

O Si O

H

O

H

Rx-ID: 31162024 View in Reaxys 43/90 Yield

Conditions & References With water, sodium hydroxide in tetrahydrofuran, methanol, T= 0 - 20 °C , Inert atmosphere, optical yield given as percent ee Addis, Daniele; Shaikh, Nadim; Zhou, Shaolin; Das, Shoubhik; Junge, Kathrin; Beller, Matthius; Chemistry - An Asian Journal; vol. 5; nb. 7; (2010); p. 1687 - 1691 View in Reaxys

O

O

HO

HO

O

O

H

H

Rx-ID: 1697038 View in Reaxys 44/90 Yield 47 %

Conditions & References With Candida antarctica lipase B in 1,1,1,2-tetrafluoroethane, Time= 72h, T= 25 °C , Resolution of racemate, Enzymatic reaction, optical yield given as percent ee Ball, Anthony J.; Corr, Stuart; Micklefield, Jason; Tetrahedron Letters; vol. 50; nb. 26; (2009); p. 3543 - 3546 View in Reaxys

46 %

With 4 A molecular sieve in hexane, Time= 5.5h, T= 25 °C , lipase from Pseudomonas sp.

Burgess, Kevin; Jennings, Lee D.; Journal of the American Chemical Society; vol. 113; nb. 16; (1991); p. 6129 - 6139 View in Reaxys With Burkholderia cepacia lipase immobilized on ceramic particles in tetrahydrofuran, Time= 48h, T= 20 °C Kiss, Violetta; Egri, Gabriella; Balint, Jozsef; Ling, Istvan; Barkoczi, Jozsef; Fogassy, Elemer; Tetrahedron Asymmetry; vol. 17; nb. 15; (2006); p. 2220 - 2234 View in Reaxys

281 mg

With Pseudomonas cepacia lipase in di-isopropyl ether, Time= 4h, T= 20 °C Kerti, Gabor; Kurtan, Tibor; Illyes, Tuende-Zita; Koever, Katalin E.; Solyom, Sandor; Pescitelli, Gennaro; Fujioka, Naoko; Berova, Nina; Antus, Sandor; European Journal of Organic Chemistry; nb. 2; (2007); p. 296 - 305 View in Reaxys

O

O

HO

HO

H

H

Rx-ID: 28590413 View in Reaxys 45/90 Yield

Conditions & References With water in acetonitrile, Time= 24h, T= 25 °C , pH= 7, aq. phosphate buffer, optical yield given as percent ee Bonomi, Paolo; Cairoli, Paola; Ubiali, Daniela; Morelli, Carlo F.; Filice, Marco; Nieto, Ines; Pregnolato, Massimo; Manitto, Paolo; Terreni, Marco; Speranza, Giovanna; Tetrahedron Asymmetry; vol. 20; nb. 4; (2009); p. 467 - 472 View in Reaxys

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Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

27/41

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HO

H

O B O

Rx-ID: 28595835 View in Reaxys 46/90 Yield

Conditions & References With sodium hydroxide, dihydrogen peroxide in tetrahydrofuran, water, T= 0 °C Lee, Yunmi; Hoveyda, Amir H.; Journal of the American Chemical Society; vol. 131; (2009); p. 3160 - 3161 View in Reaxys

HO

O H

Rx-ID: 11347911 View in Reaxys 47/90 Yield

Conditions & References Reaction Steps: 5 1.1: L-proline / dimethylsulfoxide / 2 h / 25 °C 1.2: 86 percent / NaBH4 / dimethylsulfoxide; methanol / 0.17 h / 0 °C 2.1: 88 percent / hydrogen / Pd/C / methanol / 12 h / 760.05 Torr 3.1: triethylamine / CH2Cl2 / 1 h / 0 °C 4.1: 0.33 g / sodium hydride / dimethylformamide; various solvent(s) / 0.5 h / 0 °C 5.1: 92 percent / LiAlH4 / tetrahydrofuran / 2 h / Heating With lithium aluminium tetrahydride, hydrogen, sodium hydride, triethylamine, L-proline, palladium on activated charcoal in tetrahydrofuran, methanol, dichloromethane, dimethyl sulfoxide, N,N-dimethyl-formamide Talluri, Siva Kumar; Sudalai, Arumugam; Tetrahedron; vol. 63; nb. 39; (2007); p. 9758 - 9763 View in Reaxys

HO

HO H

OH

Rx-ID: 11378921 View in Reaxys 48/90 Yield

Conditions & References Reaction Steps: 3 1: triethylamine / CH2Cl2 / 1 h / 0 °C 2: 0.33 g / sodium hydride / dimethylformamide; various solvent(s) / 0.5 h / 0 °C 3: 92 percent / LiAlH4 / tetrahydrofuran / 2 h / Heating With lithium aluminium tetrahydride, sodium hydride, triethylamine in tetrahydrofuran, dichloromethane, N,N-dimethyl-formamide Talluri, Siva Kumar; Sudalai, Arumugam; Tetrahedron; vol. 63; nb. 39; (2007); p. 9758 - 9763 View in Reaxys

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Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

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HO

O S O

H

O

OH

Rx-ID: 11384142 View in Reaxys 49/90 Yield

Conditions & References Reaction Steps: 2 1: 0.33 g / sodium hydride / dimethylformamide; various solvent(s) / 0.5 h / 0 °C 2: 92 percent / LiAlH4 / tetrahydrofuran / 2 h / Heating With lithium aluminium tetrahydride, sodium hydride in tetrahydrofuran, N,N-dimethyl-formamide Talluri, Siva Kumar; Sudalai, Arumugam; Tetrahedron; vol. 63; nb. 39; (2007); p. 9758 - 9763 View in Reaxys

HO

O N H

H

HO

Rx-ID: 11389302 View in Reaxys 50/90 Yield

Conditions & References Reaction Steps: 4 1: 88 percent / hydrogen / Pd/C / methanol / 12 h / 760.05 Torr 2: triethylamine / CH2Cl2 / 1 h / 0 °C 3: 0.33 g / sodium hydride / dimethylformamide; various solvent(s) / 0.5 h / 0 °C 4: 92 percent / LiAlH4 / tetrahydrofuran / 2 h / Heating With lithium aluminium tetrahydride, hydrogen, sodium hydride, triethylamine, palladium on activated charcoal in tetrahydrofuran, methanol, dichloromethane, N,N-dimethyl-formamide Talluri, Siva Kumar; Sudalai, Arumugam; Tetrahedron; vol. 63; nb. 39; (2007); p. 9758 - 9763 View in Reaxys

O S

O

HO

B O

H

Cl

Rx-ID: 10156150 View in Reaxys 51/90 Yield

Conditions & References Stage 1: With ethylmagnesium chloride in tetrahydrofuran, toluene, Time= 0.8h, T= -78 °C Stage 2: in tetrahydrofuran, toluene, Heating Stage 3: With sodium hydroxide, dihydrogen peroxide in various solvents, Time= 3h, T= 0 - 20 °C Blakemore, Paul R.; Marsden, Stephen P.; Vater, Huw D.; Organic Letters; vol. 8; nb. 4; (2006); p. 773 - 776 View in Reaxys

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29/41

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HO

HO

O

O

H O

O

Rx-ID: 10286638 View in Reaxys 52/90 Yield

Conditions & References With Burkholderia cepacia lipase immobilized on ceramic particles in hexane, Time= 48h, T= 20 °C Kiss, Violetta; Egri, Gabriella; Balint, Jozsef; Ling, Istvan; Barkoczi, Jozsef; Fogassy, Elemer; Tetrahedron Asymmetry; vol. 17; nb. 15; (2006); p. 2220 - 2234 View in Reaxys

O

HO S

H

Rx-ID: 12655371 View in Reaxys 53/90 Yield

Conditions & References Reaction Steps: 2 1.1: 16 percent / potassium carbonate; N-chlorosuccinimide / CH2Cl2 / 140 h / 20 °C 2.1: EtMgCl / toluene; tetrahydrofuran / 0.8 h / -78 °C 2.2: toluene; tetrahydrofuran / Heating 2.3: 56 percent / sodium hydroxide; hydrogen peroxide / various solvents / 3 h / 0 - 20 °C With N-chloro-succinimide, ethylmagnesium chloride, potassium carbonate in tetrahydrofuran, dichloromethane, toluene Blakemore, Paul R.; Marsden, Stephen P.; Vater, Huw D.; Organic Letters; vol. 8; nb. 4; (2006); p. 773 - 776 View in Reaxys

HO

H

Rx-ID: 7645393 View in Reaxys 54/90 Yield

Conditions & References Bird,C.W.; Tetrahedron; vol. 18; (1962); p. 1 - 5 View in Reaxys 6 Patent; POSTECH FOUNDATION; POSCO; WO2005/9935; (2005); (A1) English View in Reaxys 16 Patent; POSTECH FOUNDATION; POSCO; WO2005/9935; (2005); (A1) English View in Reaxys

O

OH HO

S

H

Rx-ID: 9848644 View in Reaxys 55/90 Yield

Conditions & References With tert.-butyl lithium in tetrahydrofuran, Time= 0.166667h, T= -78 °C

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30/41

2018-05-22 18:45:00

Garcia Ruano, Jose L.; Fernandez-Ibanez, M. Angeles; Maestro, M. Carmen; Rodriguez-Fernandez, M. Mercedes; Journal of Organic Chemistry; vol. 70; nb. 5; (2005); p. 1796 - 1801 View in Reaxys

O

HO

O

O

HO

O

HO

O

H

O

H

H

H

Rx-ID: 10025556 View in Reaxys 56/90 Yield

Conditions & References With Candida antarctica lipase B, chlorodicarbonyl(1,2,3,4,5-pentaphenylcyclopentadienyl)ruthenium(II), potassium tert-butylate, sodium carbonate in tetrahydrofuran, toluene, Time= 6h, T= 20 °C , Title compound not separated from byproducts Martin-Matute, Belen; Edin, Michaela; Bogar, Krisztian; Kaynak, F. Betuel; Baeckvall, Jan-E.; Journal of the American Chemical Society; vol. 127; nb. 24; (2005); p. 8817 - 8825 View in Reaxys

HO

O

HO

S O

O

H

Rx-ID: 10160602 View in Reaxys 57/90 Yield

Conditions & References With Sulfolobus acidocaldarius DSM 639 in phosphate buffer Wallner, Sabine R.; Nestl, Bettina M.; Faber, Kurt; Organic and Biomolecular Chemistry; vol. 3; nb. 14; (2005); p. 2652 2656 View in Reaxys

O

O HO

S

H

Rx-ID: 13152694 View in Reaxys 58/90 Yield

Conditions & References Reaction Steps: 2 1: L-Selectride / tetrahydrofuran / 1 h / -78 °C 2: 67 percent / tert-butyllithium / tetrahydrofuran / 0.17 h / -78 °C With tert.-butyl lithium, L-Selectride in tetrahydrofuran Garcia Ruano, Jose L.; Fernandez-Ibanez, M. Angeles; Maestro, M. Carmen; Rodriguez-Fernandez, M. Mercedes; Journal of Organic Chemistry; vol. 70; nb. 5; (2005); p. 1796 - 1801 View in Reaxys

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HO

OH

HO

H H HO

H

H

Rx-ID: 9717265 View in Reaxys 59/90 Yield

Conditions & References Stage 1: With (S)-2-methyl-quinazolinap rhodium, benzo[1,3,2]dioxaborole in tetrahydrofuran, Time= 2h, T= 0 °C Stage 2: With sodium hydroxide, dihydrogen peroxide in tetrahydrofuran, ethanol, T= 0 - 20 °C , Title compound not separated from byproducts Connolly, David J.; Lacey, Patrick M.; McCarthy, Mary; Saunders, Cormac P.; Carroll, Anne-Marie; Goddard, Richard; Guiry, Patrick J.; Journal of Organic Chemistry; vol. 69; nb. 20; (2004); p. 6572 - 6589 View in Reaxys Stage 1: With (R)-2-tert-butyl-quinazolinap rhodium, benzo[1,3,2]dioxaborole in tetrahydrofuran, Time= 4h, T= 0 °C Stage 2: With sodium hydroxide, dihydrogen peroxide in tetrahydrofuran, ethanol, T= 0 - 20 °C , Title compound not separated from byproducts Connolly, David J.; Lacey, Patrick M.; McCarthy, Mary; Saunders, Cormac P.; Carroll, Anne-Marie; Goddard, Richard; Guiry, Patrick J.; Journal of Organic Chemistry; vol. 69; nb. 20; (2004); p. 6572 - 6589 View in Reaxys

HO

OH

HO

H H HO

H

H

Rx-ID: 9721780 View in Reaxys 60/90 Yield

Conditions & References Stage 1: With (R)-2-tert-butyl-quinazolinap rhodium, benzo[1,3,2]dioxaborole in tetrahydrofuran, Time= 2h, T= 20 °C Stage 2: With sodium hydroxide, dihydrogen peroxide in tetrahydrofuran, ethanol, T= 0 - 20 °C , Title compound not separated from byproducts Connolly, David J.; Lacey, Patrick M.; McCarthy, Mary; Saunders, Cormac P.; Carroll, Anne-Marie; Goddard, Richard; Guiry, Patrick J.; Journal of Organic Chemistry; vol. 69; nb. 20; (2004); p. 6572 - 6589 View in Reaxys

Se

HO

HO

H

H

HO

Rx-ID: 9809798 View in Reaxys 61/90 Yield

Conditions & References Stage 1: With vinyl acetate, immobilized Novozym 435(R) Candida antarctica lipase-B in hexane, Time= 72h, T= 32 °C Stage 2: With triphenylstannane, 1,1'-azobis(1-cyanocyclohexanenitrile) in hexane, toluene, Time= 4h, Heating, Title compound not separated from byproducts Costa, Carlos E.; Clososki, Giuliano C.; Barchesi, Henrique B.; Zanotto, Sandra P.; Nascimento, M. Graca; Comasseto, Joao V.; Tetrahedron Asymmetry; vol. 15; nb. 24; (2004); p. 3945 - 3954 View in Reaxys

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HO

HO

Se

H

H

HO

Rx-ID: 9822582 View in Reaxys 62/90 Yield

Conditions & References With triphenylstannane, 1,1'-azobis(1-cyanocyclohexanenitrile) in toluene, Time= 4h, Heating Costa, Carlos E.; Clososki, Giuliano C.; Barchesi, Henrique B.; Zanotto, Sandra P.; Nascimento, M. Graca; Comasseto, Joao V.; Tetrahedron Asymmetry; vol. 15; nb. 24; (2004); p. 3945 - 3954 View in Reaxys

–O

–O

O S

O

HO

O S

Na + O

O

Na + O

H

Rx-ID: 9986924 View in Reaxys 63/90 Yield

Conditions & References With whole cells of Sulfolobus acidocaldarius DSM 639 in phosphate buffer, T= 20 °C , pH= 2 - 3, Microbiological reaction Wallner, Sabine R.; Nestl, Bettina M.; Faber, Kurt; Organic Letters; vol. 6; nb. 26; (2004); p. 5009 - 5010 View in Reaxys

HO

O H

Rx-ID: 9547977 View in Reaxys 64/90 Yield

Conditions & References With formic acid, triethylamine, Pd0-EnCatTM in ethyl acetate, Time= 3h, T= 23 °C Ley, Steven V.; Mitchell, Claire; Pears, David; Ramarao, Chandrashekar; Yu, Jin-Quan; Zhou, Wuzong; Organic Letters; vol. 5; nb. 24; (2003); p. 4665 - 4668 View in Reaxys Reaction Steps: 2 1: aq. K2CO3 / Heating 2: (i) PBr5, CHCl3, (ii) Zn-Cu, aq. HCl With potassium carbonate Fischer,F.; Chemische Berichte; vol. 94; (1961); p. 893 - 901 View in Reaxys

O

O

O

HO

H

O

HO

O

O

H

H

H

Rx-ID: 2070658 View in Reaxys 65/90

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Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

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Yield

Conditions & References With water, Time= 168h, T= 30 °C , asymmetric hydrolysis and resolution by Pseudomonas cepacia, Product distribution Horiuchi, Kenichi; Kobashi, Kazunori; Nagata, Hidetomo; Satoh, Toshinobu; Suemitsu, Rikisaku; Bioscience, Biotechnology, and Biochemistry; vol. 58; nb. 7; (1994); p. 1330 - 1331 View in Reaxys With recombinant pig liver esterase in phosphate buffer, Time= 2h, pH= 7.5, Enzymatic reaction Musidlowska, Anna; Lange, Stefan; Bornscheuer, Uwe T.; Angewandte Chemie - International Edition; vol. 40; nb. 15; (2001); p. 2851 - 2853 View in Reaxys

HO

M g

Br

H

Rx-ID: 15086971 View in Reaxys 66/90 Yield

Conditions & References Reaction Steps: 2 1.1: n-BuLi / tetrahydrofuran / 0.5 h / -30 °C 1.2: 68 percent / tetrahydrofuran / 1 h / 20 °C 2.1: Sphingomonas paucimobilis NCIMB 8195 / dimethylformamide; H2O; various solvent(s) / 120 h With n-butyllithium, Sphingomonas paucimobilis NCIMB 8195 in tetrahydrofuran, water, N,N-dimethyl-formamide Allan; Carnell; Journal of Organic Chemistry; vol. 66; nb. 19; (2001); p. 6495 - 6497 View in Reaxys

18OH

H

HO

HO

18O

H

18O

18O

Rx-ID: 5140532 View in Reaxys 67/90 Yield

Conditions & References With methane, oxygen in gaseous matrix, T= 25 °C , Irradiation, other temperatures, Product distribution, Kinetics, Mechanism Speranza, Maurizio; Filippi, Antonello; Chemistry - A European Journal; vol. 5; nb. 3; (1999); p. 834 - 844 View in Reaxys

HO

HO

O

H Cl

O

HO

H

O

O

O

Rx-ID: 5152223 View in Reaxys 68/90

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Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

34/41

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Yield

Conditions & References With 4 A molecular sieve, chiral diamine, triethylamine in dichloromethane, Time= 3h, T= -78 °C , Yield given, Yields of byproduct given Sano, Tomohumi; Imai, Keisuke; Ohashi, Kousaburo; Oriyama, Takeshi; Chemistry Letters; nb. 3; (1999); p. 265 - 266 View in Reaxys

O

HO

O

O

HO

O

H

Cl

H

Rx-ID: 5195143 View in Reaxys 69/90 Yield

Conditions & References

60 %

With (.eta.5-indenyl)ruthenium(bis(triphenylphosphine))chloride, Pseudomonas cepocia lipase, triethylamine, Time= 43h, T= 60 °C , Enzymatic reaction, Esterification, resolution of racemate, Title compound not separated from byproducts Koh, Jeong Hwan; Jung, Hyun Min; Kim, Mahn-Joo; Park, Jaiwook; Tetrahedron Letters; vol. 40; nb. 34; (1999); p. 6281 6284 View in Reaxys

HO

O H

Br

Rx-ID: 16607429 View in Reaxys 70/90 Yield

Conditions & References Reaction Steps: 3 1: 91 percent / D-glucose, fresh baker's yeast, XAD1180 resin / H2O / 48 h / 25 °C 2: 73 percent / aq. NaOH / 0.75 h / 65 °C 3: 86 percent / LiAlH4 / diethyl ether / 2 h / Heating With sodium hydroxide, lithium aluminium tetrahydride, D-glucose, fresh baker's yeast, XAD1180 resin in diethyl ether, water D'Arrigo, Paola; Lattanzio, Maria; Fantoni, Giuseppe Pedrocchi; Servi, Stefano; Tetrahedron Asymmetry; vol. 9; nb. 22; (1998); p. 4021 - 4026 View in Reaxys Reaction Steps: 3 1: 86 percent / Baker's yeast, resin XAD 1180, D-glucose / H2O / 24 h / 28 °C 2: 73 percent / NaOH / 65 °C 3: 86 percent / LiAlH4 / diethyl ether / 2 h / Heating With sodium hydroxide, lithium aluminium tetrahydride, baker's yeast, D-glucose, resin XAD 1180 in diethyl ether, water D'Arrigo, Paola; Fuganti, Claudio; Pedrocchi Fantoni, Giuseppe; Servi, Stefano; Tetrahedron; vol. 54; nb. 49; (1998); p.

15017 - 15026 View in Reaxys Reaction Steps: 3 1: Baker's yeast, D-glucose / H2O / 24 h / 28 °C 2: 73 percent / NaOH / 65 °C 3: 86 percent / LiAlH4 / diethyl ether / 2 h / Heating With sodium hydroxide, lithium aluminium tetrahydride, baker's yeast, D-glucose in diethyl ether, water D'Arrigo, Paola; Fuganti, Claudio; Pedrocchi Fantoni, Giuseppe; Servi, Stefano; Tetrahedron; vol. 54; nb. 49; (1998); p.

15017 - 15026 View in Reaxys

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2018-05-22 18:45:00

HO

HO Br

H

H

Rx-ID: 16612852 View in Reaxys 71/90 Yield

Conditions & References Reaction Steps: 2 1: 73 percent / aq. NaOH / 0.75 h / 65 °C 2: 86 percent / LiAlH4 / diethyl ether / 2 h / Heating With sodium hydroxide, lithium aluminium tetrahydride in diethyl ether D'Arrigo, Paola; Lattanzio, Maria; Fantoni, Giuseppe Pedrocchi; Servi, Stefano; Tetrahedron Asymmetry; vol. 9; nb. 22; (1998); p. 4021 - 4026 View in Reaxys Reaction Steps: 2 1: 73 percent / NaOH / 65 °C 2: 86 percent / LiAlH4 / diethyl ether / 2 h / Heating With sodium hydroxide, lithium aluminium tetrahydride in diethyl ether D'Arrigo, Paola; Fuganti, Claudio; Pedrocchi Fantoni, Giuseppe; Servi, Stefano; Tetrahedron; vol. 54; nb. 49; (1998); p.

15017 - 15026 View in Reaxys

HO OH

H N N N

N

Rx-ID: 4643190 View in Reaxys 72/90 Yield

Conditions & References With hydrogen, palladium on activated charcoal in ethanol, Time= 48h Donzelli, Fabio; Fuganti, Claudio; Mendozza, Monica; Pedrocchi-Fantoni, Giuseppe; Servi, Stefano; Zucchi, Gioia; Tetrahedron Asymmetry; vol. 7; nb. 11; (1996); p. 3129 - 3134 View in Reaxys

O

HO

H

OH

Rx-ID: 17420114 View in Reaxys 73/90 Yield

Conditions & References Reaction Steps: 3 1: baker's yeast / ethanol / 48 h / 25 °C 2: 57 percent / K2CO3 / acetone / 48 h 3: 95 percent / H2 / 10percent Pd/C / ethanol / 48 h With baker's yeast, hydrogen, potassium carbonate, palladium on activated charcoal in ethanol, acetone Donzelli, Fabio; Fuganti, Claudio; Mendozza, Monica; Pedrocchi-Fantoni, Giuseppe; Servi, Stefano; Zucchi, Gioia; Tetrahedron Asymmetry; vol. 7; nb. 11; (1996); p. 3129 - 3134 View in Reaxys

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HO

HO

H

OH

Rx-ID: 17451239 View in Reaxys 74/90 Yield

Conditions & References Reaction Steps: 2 1: 57 percent / K2CO3 / acetone / 48 h 2: 95 percent / H2 / 10percent Pd/C / ethanol / 48 h With hydrogen, potassium carbonate, palladium on activated charcoal in ethanol, acetone Donzelli, Fabio; Fuganti, Claudio; Mendozza, Monica; Pedrocchi-Fantoni, Giuseppe; Servi, Stefano; Zucchi, Gioia; Tetrahedron Asymmetry; vol. 7; nb. 11; (1996); p. 3129 - 3134 View in Reaxys

N

HO

O H

O

O OH

N

Rx-ID: 4187999 View in Reaxys 75/90 Yield

Conditions & References in methanol, water, penicillin G acylase in pH 8 phosphate buffer, Rate constant Pohl; Waldmann; Tetrahedron Letters; vol. 36; nb. 17; (1995); p. 2963 - 2966 View in Reaxys

HO

O

O

H

HO

O

O

O

H

O

H

Rx-ID: 2204416 View in Reaxys 76/90 Yield

Conditions & References With water, Time= 168h, T= 30 °C , asymmetric hydrolysis and resolution by Pseudomonas cepacia, Product distribution Horiuchi, Kenichi; Kobashi, Kazunori; Nagata, Hidetomo; Satoh, Toshinobu; Suemitsu, Rikisaku; Bioscience, Biotechnology, and Biochemistry; vol. 58; nb. 7; (1994); p. 1330 - 1331 View in Reaxys

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Cl

Cl

H

Cl

HO

HO

O

H

HO

H

Rx-ID: 3962197 View in Reaxys 77/90 Yield

Conditions & References Time= 24h, Bakers' yeast, Yield given. Yields of byproduct given Besse; Renard; Veschambre; Tetrahedron Asymmetry; vol. 5; nb. 7; (1994); p. 1249 - 1268 View in Reaxys

O

HO

HO

HO

O

H

H

H

Rx-ID: 1983184 View in Reaxys 78/90 Yield

Conditions & References Yield given. Yields of byproduct given. Title compound not separated from byproducts Bianchi, Daniele; Cesti, Pietro; Battistel, Ezio; Journal of Organic Chemistry; vol. 53; nb. 23; (1988); p. 5531 - 5534 View in Reaxys

HO

O

O

O

O

HO

O O

O

H

H

H

Rx-ID: 2346541 View in Reaxys 79/90 Yield

Conditions & References in benzene, Time= 30h, T= 21 °C , lipase Amano P/Celite 577, Yield given. Yields of byproduct given. Title compound not separated from byproducts Bianchi, Daniele; Cesti, Pietro; Battistel, Ezio; Journal of Organic Chemistry; vol. 53; nb. 23; (1988); p. 5531 - 5534 View in Reaxys

HO

HO

O

O

H O

O

O

Rx-ID: 2940025 View in Reaxys 80/90 Yield 39 %

Conditions & References in benzene, Time= 10h, T= 21 °C , lipase Amano P/Celite 577, Yields of byproduct given Bianchi, Daniele; Cesti, Pietro; Battistel, Ezio; Journal of Organic Chemistry; vol. 53; nb. 23; (1988); p. 5531 - 5534 View in Reaxys

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Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

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O

HO

O

H

H

Rx-ID: 3967177 View in Reaxys 81/90 Yield

Conditions & References With potassium carbonate in methanol, Ambient temperature Laumen, Kurt; Schneider, Manfred P.; Journal of the Chemical Society, Chemical Communications; (1988); p. 598 - 600 View in Reaxys

HO

O Cl

H

O

Rx-ID: 4024758 View in Reaxys 82/90 Yield

Conditions & References With potassium carbonate in methanol, Ambient temperature Laumen, Kurt; Schneider, Manfred P.; Journal of the Chemical Society, Chemical Communications; (1988); p. 598 - 600 View in Reaxys

O

O

HO

H

Rx-ID: 18183742 View in Reaxys 83/90 Yield

Conditions & References Reaction Steps: 2 2: K2CO3 / methanol / Ambient temperature With potassium carbonate in methanol Laumen, Kurt; Schneider, Manfred P.; Journal of the Chemical Society, Chemical Communications; (1988); p. 598 - 600 View in Reaxys

O

HO

Cl H

O

Rx-ID: 18217526 View in Reaxys 84/90 Yield

Conditions & References Reaction Steps: 2 2: K2CO3 / methanol / Ambient temperature With potassium carbonate in methanol Laumen, Kurt; Schneider, Manfred P.; Journal of the Chemical Society, Chemical Communications; (1988); p. 598 - 600 View in Reaxys

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HO

H

SiH O

Rx-ID: 3198431 View in Reaxys 85/90 Yield

Conditions & References With hydrogen cation in water, Yield given Brunner, Henri; Reiter, Barbara; Riepl, Georg; Chemische Berichte; vol. 117; nb. 4; (1984); p. 1330 - 1354 View in Reaxys

O

HO

<2.4-dioxy-phenyl>-benzyl ketone

H

Rx-ID: 19999152 View in Reaxys 86/90 Yield

Conditions & References Reaction Steps: 2 1: <Rh(cycloocta-1,5-diene)Cl>2 / (S)-η-methyl-N-(phenyl-2-pyridinylmethylene)-phenylmethanamine (Rh:ligand = 1:9) / 46 h / 0 - 25 °C / var. of N-chelate ligands, Rh:ligand-proportion 2: H+ / H2O With hydrogen cation, chloro(1,5-cyclooctadiene)rhodium(I) dimer, (S)-1-phenyl-N-[(pyridin-2-yl)methylene]ethanamine in water Brunner, Henri; Reiter, Barbara; Riepl, Georg; Chemische Berichte; vol. 117; nb. 4; (1984); p. 1330 - 1354 View in Reaxys

H HO

H 2N

HO

HO

HO

H

H

HO

Rx-ID: 2198132 View in Reaxys 87/90 Yield

Conditions & References With sodium nitrite in perchloric acid, water, Product distribution, Mechanism Kirmse, Wolfgang; Guenther, Bernd-Rainer; Loosen, Karin; Chemische Berichte; vol. 113; nb. 6; (1980); p. 2140 - 2153 View in Reaxys

OH

H

HO

HO H

H

Rx-ID: 4307174 View in Reaxys 88/90 Yield

Conditions & References (i) PBr5, CHCl3, (ii) Zn-Cu, aq. HCl, Multistep reaction

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Fischer,F.; Chemische Berichte; vol. 94; (1961); p. 893 - 901 View in Reaxys

HO

O H

Rx-ID: 22765029 View in Reaxys 89/90 Yield

Conditions & References Reaction Steps: 2 1: aq. H2SO4 2: (i) PBr5, CHCl3, (ii) Zn-Cu, aq. HCl With sulfuric acid Fischer,F.; Chemische Berichte; vol. 94; (1961); p. 893 - 901 View in Reaxys

HO

dl-methyl-benzyl-carbinol

H

Rx-ID: 7645394 View in Reaxys 90/90 Yield

Conditions & References ueber den sauren Phthalsaeureester und dessen Brucinsalz oder Strychninsalz Pickard; Kenyon; Journal of the Chemical Society; vol. 105; (1914); p. 1124 View in Reaxys

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Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

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