The oxide anion accelerated retro-Diels-Alder reaction

Chemistry - A European Journal

Volumn 3, Issue 2, 1997, Pages 187-192

  Bunnage, Mark E ^a,b,c   Nicolaou, K C ^a,b  

^a SCRIPPS RESEARCH INSTITUTE   (United States)

^b UNIVERSITY OF CALIFORNIA   (United States)

^c PFIZER GLOBAL RESEARCH AND DEVELOPMENT   (United Kingdom)

Author keywords

Diels Alder reactions; oxide anion; pericyclic reactions; retro reactions; synthetic methods

Indexed keywords

EID: 0030889815     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/chem.19970030204     Document Type: Review

References (26)

1. For a recent review, see: A. Ichihara, Synthesis 1987, 207.
2. M. E. Bunnage, K. C. Nicolaou, Angew. Chem. Int. Ed. Engl. 1996, 35, 1110.
3. For a discussion of the mechanism of both the Diels-Alder reaction and its cycloreversion, see: J. Sauer, R. Sustmann, Angew. Chem. Int. Ed. Engl. 1980, 19, 779.
4. D. A. Evans, A. M. Golob, J. Am. Chem. Soc. 1975, 97, 4765.
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8. M. L. Steigerwald, W. A. Goddard III, D. A. Evans, J. Am. Chem. Soc. 1979, 101, 1994.
9. D. A. Evans, J. V. Nelson, J. Am. Chem. Soc. 1980, 102, 774.
10. B. K. Carpenter, Tetrahedron 1978, 34, 1877.
11. O. Papies, W. Grimme, Tetrahedron Lett. 1980, 21, 2799.
12. Although apparently unrecognised, the oxide anion acceleration of a retro-Diels-Alder reaction may have been witnessed over a decade in advance of the Grimme study, see: A. Oku, T. Kakihana, H. Hart, J. Am. Chem. Soc. 1967, 89, 4554.
13. S. Knapp, R. M. Ornaf, K. E. Rodriques, J. Am. Chem. Soc. 1983, 105, 5494.
14. T. V. RajanBabu, D. F. Eaton, T. Fukunaga, J. Org. Chem. 1983, 48, 652.
15. T. Miyashi, A. Ahmed, T. Mukai, J. Chem. Soc. Chem. Commun. 1984, 179.
16. This system has been shown to undergo a formal retro-Diets Alder reaction upon treatment with phenylmagnesium bromide, see: J. V. N. Vara Prasad, P. Iyer, C. N. Pillai, J. Org. Chem. 1982, 47, 1381. Since the corresponding potassium alkoxide does not cyclorevert (ref. [14]), the possibility that the reaction is not concerted seems likely.
17. Experimental support for carbocation acceleration of the Cope rearrangement is available, see ref. [10].
18. The acceleration of retro-Diels-Alder reactions by carbanion generation has been demonstrated in other systems, see: E. S. Bowman, G. B. Hughes, J. B. Grutzner, J. Am. Chem. Soc. 1976, 98, 8273; W Neukam, W. Grimme, Tetrahedron Lett. 1978, 25, 2201.
19. The acceleration of retro-Diels-Alder reactions by carbanion generation has been demonstrated in other systems, see: E. S. Bowman, G. B. Hughes, J. B. Grutzner, J. Am. Chem. Soc. 1976, 98, 8273; W Neukam, W. Grimme, Tetrahedron Lett. 1978, 25, 2201.
20. R. D. Miller, D. L. Dolce, Tetrahedron Lett. 1977, 38, 3329.
21. For selected reviews, see: a) K. C. Nicolaou, W.-M. Dai, Angew. Chem. Int. Ed. Engl. 1991, 30, 1387; b) K. C. Nicolaou, A. L. Smith, Acc. Chem. Res. 1992, 25, 497; c) K. C. Nicolaou, A. L. Smith, E. W. Yue, Proc. Natl. Acad. Sci. USA 1993, 90, 5881; d) A. L. Smith, K. C. Nicolaou, J. Med. Chem. 1996, 39, 2103; e) J. W. Grissom, G. U. Gunawardena, D. Klingberg, D. Huang, Tetrahedron 1996, 52, 6453; f) M. E. Maier, Synlett 1995, 13.
22. For selected reviews, see: a) K. C. Nicolaou, W.-M. Dai, Angew. Chem. Int. Ed. Engl. 1991, 30, 1387; b) K. C. Nicolaou, A. L. Smith, Acc. Chem. Res. 1992, 25, 497; c) K. C. Nicolaou, A. L. Smith, E. W. Yue, Proc. Natl. Acad. Sci. USA 1993, 90, 5881; d) A. L. Smith, K. C. Nicolaou, J. Med. Chem. 1996, 39, 2103; e) J. W. Grissom, G. U. Gunawardena, D. Klingberg, D. Huang, Tetrahedron 1996, 52, 6453; f) M. E. Maier, Synlett 1995, 13.
23. For selected reviews, see: a) K. C. Nicolaou, W.-M. Dai, Angew. Chem. Int. Ed. Engl. 1991, 30, 1387; b) K. C. Nicolaou, A. L. Smith, Acc. Chem. Res. 1992, 25, 497; c) K. C. Nicolaou, A. L. Smith, E. W. Yue, Proc. Natl. Acad. Sci. USA 1993, 90, 5881; d) A. L. Smith, K. C. Nicolaou, J. Med. Chem. 1996, 39, 2103; e) J. W. Grissom, G. U. Gunawardena, D. Klingberg, D. Huang, Tetrahedron 1996, 52, 6453; f) M. E. Maier, Synlett 1995, 13.
24. For selected reviews, see: a) K. C. Nicolaou, W.-M. Dai, Angew. Chem. Int. Ed. Engl. 1991, 30, 1387; b) K. C. Nicolaou, A. L. Smith, Acc. Chem. Res. 1992, 25, 497; c) K. C. Nicolaou, A. L. Smith, E. W. Yue, Proc. Natl. Acad. Sci. USA 1993, 90, 5881; d) A. L. Smith, K. C. Nicolaou, J. Med. Chem. 1996, 39, 2103; e) J. W. Grissom, G. U. Gunawardena, D. Klingberg, D. Huang, Tetrahedron 1996, 52, 6453; f) M. E. Maier, Synlett 1995, 13.
25. For selected reviews, see: a) K. C. Nicolaou, W.-M. Dai, Angew. Chem. Int. Ed. Engl. 1991, 30, 1387; b) K. C. Nicolaou, A. L. Smith, Acc. Chem. Res. 1992, 25, 497; c) K. C. Nicolaou, A. L. Smith, E. W. Yue, Proc. Natl. Acad. Sci. USA 1993, 90, 5881; d) A. L. Smith, K. C. Nicolaou, J. Med. Chem. 1996, 39, 2103; e) J. W. Grissom, G. U. Gunawardena, D. Klingberg, D. Huang, Tetrahedron 1996, 52, 6453; f) M. E. Maier, Synlett 1995, 13.
26. For selected reviews, see: a) K. C. Nicolaou, W.-M. Dai, Angew. Chem. Int. Ed. Engl. 1991, 30, 1387; b) K. C. Nicolaou, A. L. Smith, Acc. Chem. Res. 1992, 25, 497; c) K. C. Nicolaou, A. L. Smith, E. W. Yue, Proc. Natl. Acad. Sci. USA 1993, 90, 5881; d) A. L. Smith, K. C. Nicolaou, J. Med. Chem. 1996, 39, 2103; e) J. W. Grissom, G. U. Gunawardena, D. Klingberg, D. Huang, Tetrahedron 1996, 52, 6453; f) M. E. Maier, Synlett 1995, 13.