Simple and practical routes to enantiomerically pure 5-(Trialkylsilyl)-2-cyclohexenones

Organic Letters

Volumn 1, Issue 5, 1999, Pages 811-814

  Sarakinos, Georgios ^a   Corey, E J ^a  

^a HARVARD UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000494450     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol990805f     Document Type: Article

References (29)

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2. By Tamao-Fleming oxidation; for a review of silyl groups as masked hydroxyl equivalents see: Fleming, I.; Henning, R.; Parker, D. C.; Plaut, H. E.; Sanderson, P. E. J. J. Chem. Soc., Perkin Trans. 1 1995, 317.
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10. 3 solution.
11. For other resolutions of cyclohexanol derivatives by enantioselective acetylation under lipase catalysis see: (a) Tanikaga, R.; Morita, A. Tetrahedron Lett. 1998, 39, 635.
12. (b) Fujisawa, T.; Yamanaka, K.; Mobele, B. I.; Shimizu, M. Tetrahedron Lett. 1991, 32, 399.
13. (c) Fukazawa, T.; Hashimoto, T. Tetrahedron: Asymmetry 1993, 4, 2323.
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15. (e) Weissfloch, A. N. E.; Kazlauskas, R. J. J. Org. Chem. 1995, 60, 6959.
16. minor = 18.0 min.
17. Found for 7, >99% ee, determined as above for 5.
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20. 3).
21. 1; a = 6.5347(11) Å, b = 17.880(3) Å, c = 11.411(2) Å; α = 90°, β = 93.175(17)°, γ = 90°; Z = 4; R1(I > 2σ(I)) = 0.0380. (b) Detailed X-ray crystallographic data are available from the Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge, CB2 1EZ, U.K.
22. Corey, E. J.; Chaykovsky, M. J. Am. Chem. Soc. 1965, 87, 1353.
23. See: Lipshutz, B. H. In Organocopper Reagents: a Practical Approach; Taylor, R. J. K., Ed.; Oxford University Press: New York, 1994; pp 105-128.
24. Asaoka, M.; Shima, K.; Takei, H. J. Chem. Soc., Chem. Commun. 1988, 430.
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26. Bennetau, B.; Rajarison, F.; Dunogués, J.; Babin, P. Tetrahedron 1994, 50, 1179.
27. (-) = 17.0 min.
28. 3).
29. major = 11 min.