Stereochemical control in the silyl triflate-mediated Claisen rearrangement of allylic esters

Tetrahedron Letters

Volumn 37, Issue 17, 1996, Pages 3005-3008

  Kobayashi, Masatada ^a   Masumoto, Katsuhisa ^a   Nakai, Ei Ichi ^a   Nakai, Takeshi ^a  

^a TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CROTONIC ACID DERIVATIVE;

ARTICLE; CHIRALITY; DRUG SYNTHESIS; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0029937878     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)00485-6     Document Type: Article

References (20)

1. A visiting research fellow from Sumitomo Chemical Co., Ltd., Osaka.
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4. (c) Ireland, R. E.; Mueller, R. H.; Willard, A. K. J. Am. Chem. Soc. 1976, 98, 2868.
5. (d) Ireland, R. E.; Wilcox, C. S. Tetrahedron Lett. 1977, 2839.
6. Reviews: (a) Ziegler, F. E. Chem. Rev. 1988, 88, 1423.
7. (b) Wipf, P. Comprehensive Organic Synthesis; Trost, B. M.; Fleming, I., Eds.; Pergamon Press: New York, 1991; Vol. 5, p 827.
8. Yokozawa, T.; Nakai, T.; Ishikawa, N. Tetrahedron Lett. 1984, 25, 3991. Also see: Yokozawa, T.; Nakai, T.; Ishikawa, N. Tetrahedron Lett. 1984, 25, 3987.
9. Yokozawa, T.; Nakai, T.; Ishikawa, N. Tetrahedron Lett. 1984, 25, 3991. Also see: Yokozawa, T.; Nakai, T.; Ishikawa, N. Tetrahedron Lett. 1984, 25, 3987.
10. (a) Funk, R. L.; Olmstead, T. A.; Parvez, M. J. Am. Chem. Soc. 1988, 110, 3298, and references cited therein,
11. (b) Schreiber, S. L.; Smith, D. B. J. Org. Chem. 1989, 54, 9.
12. (c) Angle, S. R.; Amaiz, D. O. Tetrahedron Lett. 1989, 30, 515.
13. Review on C-vs. O-silylation of esters with silyl triflates: Emde, H. Synthesis 1982, 1.
14. The (Z)-selection observed here is explicable in terms of essentially the same noncyclic mechanism advanced for explaining the (Z)-selection in the metal ester enolate formations: Evans, D. A.; Nelson, J. V.; Vogel, E.; Taber, T. R. J. Am. Chem. Soc. 1981, 103, 3099.
15. For the thermal Claisen rearrangement of allylic (α-trimethylsilyl)esters: Rowley, M.; Tsukamoto. M.; Kishi, Y. J. Am. Chem. Soc. 1989, 111, 2735.
16. 2O). The stereospecificity of (R)-5 to (R)-6 is understood as a result of the (Z)-selective formation of the ketene silyl acetal followed by the Claisen shift via the usual chair-like transition state.
17. Nagatsuma, M.; Shirai, F.; Sayo, N.; Nakai, T. Chem. Lett. 1984, 1393.
18. Basha, A.; Lipton, M.; Weinreb, S. M. Tetrahedron Lett. 1977, 4171.
19. In this reaction a considerable amount of the C-silylated ester was also formed (ca. 40% yield).
20. 2, Pd/C) followed by its GLC comparison with an authentic L-isoleucine methyl ester (anti configuration).