Diels–Alder Reaction 95
The Diels–Alder reaction is the most important method for the construction of six-membered rings. For example it can be used as a step in a benzo-anellation procedure. The experimental procedure is simple, and yields are generally good; side reactions play only a minor role. 1. O. Diels, K. Alder, Justus Liebigs Ann. Chem. 1928, 460, 98–122. 2. J. A. Norton, Chem. Rev. 1942, 31, 319–523. 3. J. G. Martin, R. K. Hill, Chem. Rev. 1961, 61, 537–562. 4. W. Carruthers, Cycloaddition Reactions in Organic Synthesis, Pergamon Press, Oxford, 1990, p. 1–208. 5. D. L. Boger, S. M. Weinreb, Hetero-Diels-Alder Methodology in Organic Synthesis, Academic Press, New York, 1987. S. M. Weinreb, P. M. Scola, Chem. Rev. 1989, 89, 1525–1534. 6. A. Ichihara, Synthesis 1987, 207–222. 7. M.-C. Lasne, J.-L. Ripoll, Synthesis 1985, 121–143; M. E. Bunnage, K. C. Nicolaou, Chem. Eur. J. 1997, 3, 187–192. 8. D. Craig, Chem. Soc. Rev. 1987, 16, 187–238. 9. J. Sauer, R. Sustmann, Angew. Chem. 1980, 92, 773–801; Angew. Chem. Int. Ed. Engl. 1980, 19, 779. 10. W. Oppolzer, Angew. Chem. 1984, 96, 840–854; Angew. Chem. Int. Ed. Engl. 1984, 23, 876. 11. J. Sauer, Angew. Chem. 1967, 79, 76–94; Angew. Chem. Int. Ed. Engl. 1967, 6, 16. 12. R. B. Woodward, R. Hoffmann, Angew. Chem. 1969, 81, 797–869; Angew. Chem. Int. Ed. Engl. 1969, 8, 781. R. B. Woodward, R. Hoffmann, The Conservation of Orbital Symmetry, Academic Press, New York, 1970. 13. I. Fleming, Frontier Orbitals and Organic Chemical Reactions, Wiley, London, 1976, p. 110–142 and 161–168. 14. P. G. Gassman, D. B. Gorman, J. Am. Chem. Soc. 1990, 112, 8624–8626. 15. A. J. Fatiadi, Synthesis 1987, 749–789. 16. J. Sauer, H. Wiest, Angew. Chem. 1962, 74, 353; Angew. Chem. Int. Ed. Engl. 1962, 1, 268. 17. K. Matsumoto, A. Sera, Synthesis 1985, 999–1027. 18. L. F. Tietze, T. H¨ubsch, J. Oelze, C. Ott, W. Tost, G. W¨orner, M. Buback, Chem. Ber. 1992, 125, 2249–2258. 19. P. A. Grieco, Aldrichimica Acta, 1991, 24(3), 59–66. H. Waldmann, Angew. Chem. 1991, 103, 1335–1337; Angew. Chem. Int. Ed. Engl. 1991, 30, 1306. 20. H. B. Kagan, O. Riant, Chem. Rev. 1992, 92, 1007–1019. Y. Hayashi, J. J. Rohde, E. J. Corey, J. Am. Chem. Soc. 1996, 118, 5502–5503. 21. H. Hopf, G. Weber, K. Menke, Chem. Ber. 1980, 113, 531–541. 22. E. Ciganek, Org. React. 1984, 32, 1–374. 23. G. Brieger, J. N. Bennett, Chem. Rev. 1980, 80, 63–97. 24. R. L. Funk, K. P. C. Vollhardt, Chem. Soc. Rev. 1980, 9, 41–62. 25. W.-D. Fessner, C. Grund, H. Prinzbach, Tetrahedron Lett. 1989, 30, 3133– 3136. 26. L. F. Tietze, U. Beifuss, Angew. Chem. 1993, 105, 137–170; Angew. Chem. Int. Ed. Engl. 1993, 32, 131. 27. L. M. Stephenson, D. E. Smith, S. P. Current, J. Org. Chem. 1982, 47, 4170.