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

Authors
Dambrin, V Villieras, M Janvier, P Toupet, L Amri, H Lebreton, J Villieras, J
Citation
V. Dambrin et al., 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, TETRAHEDRON, 57(11), 2001, pp. 2155-2170
Citations number
29
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON
ISSN journal
00404020 → ACNP
Volume
57
Issue
11
Year of publication
2001
Pages
2155 - 2170
Database
ISI
SICI code
0040-4020(20010310)57:11<2155:CMHDCA>2.0.ZU;2-J
Abstract
The conjugate addition of magnesium cuprates to various 2-silyloxycyclopent ene and 2-silyloxycyclohexene carboxylates leads diastereoserectively to re lated 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 enolat es. Attempts to rationalise our results are discussed. (C) 2001 Elsevier Sc ience Ltd. All rights reserved.