Copper(I) mediated highly diastereoselective conjugate addition of Grignard reagents to functionalised cycloalkenols: a general and efficient route for the stereoselective synthesis of 5-and 6-membered ring trisubstituted cycloalkanols

The conjugate addition of magnesium cuprates to various 2-silyloxycyclopentene and 2-silyloxycyclohexene carboxylates leads diastereoserectively to related syn-anti cyclopentanols and cyclohexanols in fair overall yields. The p-elimination occurring with free hydroxylic derivatives is also partially...

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Bibliographic Details
Published inTetrahedron Vol. 57; no. 11; pp. 2155 - 2170
Main Authors Dambrin, Villieras, M, Janvier, P, Toupet, L, Amri, H, Lebreton, J, Villieras, J
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier 10.03.2001
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
Michael addition
ORGANIC-SYNTHESIS
S(N)2
beta-elimination
ESTERS
Grignard reagents
WITTIG-HORNER REACTION
CARBONYL-COMPOUNDS
diastereoselectivity
organocuprates
conjugate addition
DERIVATIVES
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Summary:The conjugate addition of magnesium cuprates to various 2-silyloxycyclopentene and 2-silyloxycyclohexene carboxylates leads diastereoserectively to related syn-anti cyclopentanols and cyclohexanols in fair overall yields. The p-elimination occurring with free hydroxylic derivatives is also partially or totally avoided by concomitant in situ trapping of the generated enolates. Attempts to rationalise our results are discussed. (C) 2001 Elsevier Science Ltd. All rights reserved.
ISSN:0040-4020
DOI:10.1016/S0040-4020(01)00044-8