Stereoselective introduction of a trifluoromethyl group into 1,5-dicarbonyl compounds via Michael addition reaction

Reviews on Heteroatom Chemistry

Volumn 14, Issue , 1996, Pages 165-182

  Shinohara, Noriyasu ^a   Yamazaki, Takashi ^a   Kitazume, Tomoya ^a  

^a TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

Asymmetric synthesis; F Li interaction; Michael addition reaction; Oxazolidinone; Trifluoromethyl group

Indexed keywords

EID: 0008911590     PISSN: 09156151     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Review

References (43)

1. T. Kitazume and T. Yamazaki: Effect of the Fluorine Atom on Stereocontrolled Synthesis, in Selective Fluorination in Organic and Bioorganic Chemistry, (Ed) J. T. Welch (Am. Chem. Soc., Washington, D.C., 1991) Chap. 2, pp. 175-185 and references cited therein.
2. O. Takahashi, K. Furuhashi, M. Fukumasa and T. Hirai: Tetrahedron Lett. 31 7031-7034 (1990).
3. D. A. Oare and C. H. Heathcock: Top. Stereochem. 19 227-407 (1989).
4. P. Perlmutter: Conjugate Addition Reactions in Organic Synthesis (Pergamon Press, Oxford, 1992).
5. M. Yamaguchi, M. Tsukamoto and I. Hirao: Chem. Lett. 375-376 (1984).
6. M. Yamaguchi: J. Synth. Org. Chem. Jpn. 44 405-420 (1986).
7. M. Yamaguchi, M. Tsukamoto, S. Tanaka and I. Hirao: Tetrahedron Lett. 25 5661-5664 (1984).
8. D. A. Oare and C. H. Heathcock: J. Org. Chem. 55 157-172 (1990).
9. A. Bernardi, A. M. Capelli, A. Cassinari, A. Comotti, C. Gennari and C. Scolastico: J. Org. Chem. 57 7029-7034 (1992).
10. T. Fuchikami, Y. Shibata and Y. Suzuki: Tetrahedron Lett. 27 3173-3176 (1986).
11. T. Kitazume, T. Ohnogi, H. Miyauchi, T. Yamazaki and S. Watanabe: J. Org. Chem. 54 5630-5632 (1989).
12. J. P. Bégué, D. Bonnet-Delpon and M. H. Rock: Synlett 659-660 (1995).
13. G. W. Klumpp, A. J. C. Mierop, J. J. Vrielink, A. Brugman and M. Schakel: J. Am. Chem. Soc. 107 6740-6742 (1985) and references cited therein.
14. V. Martin, H. Molines and C. Wakselman: J. Org. Chem. 57 5530-5532 (1992).
15. Semiempirical molecular orbital calculation was performed by MOPAC v 6.10 (AM1) implemented in the CAChe Work system (SONY/Tektronix Corporation) for the conformers obtained by the rigid search method, followed by their optimization by the eigenvector by the minimization (EF) method with the extra keyword "PRECISE". The final gradient norm was less than 0.01 kcal/Å.
16. N. Shinohara, J. Haga, T. Yamazaki, T. Kitazume and S. Nakamura: J. Org. Chem. 60 4363-4374 (1995).
17. G. Stork, A. Y. M. Leong and A. M. Touzin: J. Org. Chem. 41 3491-3493 (1976).
18. A. van der Werf and R. M. Kellogg: Tetrahedron Lett. 32 3727-3730 (1991).
19. M. Yamaguchi, K. Hasebe, S. Tanaka and T. Minami: Tetrahedron Lett. 27 959-962 (1986).
20. Steric effect of the trifluoromethyl group was defined as similar to that of the iPr group. See G. Bott, L. D. Field and S. Sternhell: J. Am. Chem. Soc. 102 5618-5626 (1980).
21. R. Häner, T. Laube and D. Seebach: J. Am. Chem. Soc. 107 5396-5403 (1985).
22. N. E. Schore and E. G. Rowley: J. Am. Chem. Soc. 110 5224-5225 (1988).
23. M. Casey, A. M. Manage and R. S. Gairns: Tetrahedron Lett. 30 6919-6922 (1989).
24. For a review of the Michael addition of enamines, see D. A. Oare and C. H. Heathcock: Top. Stereochem. 20 87-170 (1991).
25. T. Yamazaki, S. Hiraoka and T. Kitazume: J. Org. Chem. 59 5100-5103 (1994).
26. For a review of chelation- and non-chelation-controlled additions tochiral alkoxy carbonyl compounds, see M. T. Reetz: Angew. Chem., Int. Ed. Engl. 23 556-569 (1984).
27. D. A. Oare, M. A. Henderson, M. A. Sanner and C. H. Heathcock: J. Org. Chem. 55 132-157 (1990).
28. I. Fleming: Frontier Orbitals and Organic Chemical Reactions (John Wiley and Sons, Chichester, 1976).
29. T.-L. Ho: Hard and Soft Acids and Bases, Principle in Organic Chemistry (Academic Press, Inc., New York, 1977) Chap. 7.
30. E. J. Corey and R. T. Peterson: Tetrahedron Lett. 26 5025-5028 (1985).
31. T. Yura, N. Iwasawa and T. Mukaiyama: Chem. Lett. 1021-1024 (1988).
32. D. A. Evans: Asymmetric Synthesis (Ed.) J. D. Morrison (Academic Press, New York, 1984) 3, Chap. 1, pp. 2-110.
33. D. A. Evans: Aldrichim. Acta 15 23-32 (1982).
34. D. A. Evans, M. D. Ennis and D. J. Mathre: J. Am. Chem. Soc. 104 1737-1739 (1982).
35. D. A. Evans, J. Bartroli and T. L. Shih: J. Am. Chem. Soc. 103 2127-2129 (1981).
36. D. A. Evans, T. C. Britton and J. A. Ellman: Tetrahedron Lett. 28 6141-6144 (1987).
37. D. A. Evans, M. T. Bilodean, T. C. Somers, J. Clardy, D. Cherry and Y. Kato: J. Org. Chem. 56 5750-5752 (1991).
38. S. Kanemasa, H. Suenaga and K. Onimura: J. Org. Chem. 59 6949-6954 (1994).
39. N. A. Porter, J. D. Bruhnke, W.-X. Wu, I. J. Rosenstein and R. A. Breyer: J. Am. Chem. Soc. 113 7788-7790 (1991).
40. D. Askin, M. A. Wallace, J. P. Vacca, R. A. Reamer, R. P. Volante and I. Shinkai: J. Org. Chem. 57 2771-2773 (1992).
41. Y. Narukawa, K. N. Juneau, D. Snustad, D. B. Miller and L. S. Hegedus: J. Org. Chem. 57 5453-5462 (1992).
42. N. A. Porter, T. R. Allen and R. A. Breyer: J. Am. Chem. Soc. 114 7676-7683 (1992).
43. D. M. Scott, A. T. McPhail and N. A. Porter: J. Org. Chem. 58 1178-1186 (1993).