COPPER(I) MEDIATED HIGHLY DIASTEREOSELECTIVE CONJUGATE ADDITION OF GRIGNARD-REAGENTS TO 2-SILYLOXYCYCLOPENTENECARBOXYLATES

Authors
DAMBRIN V VILLIERAS M MOREAU C AMRI H TOUPET L VILLIERAS J
Citation
V. Dambrin et al., COPPER(I) MEDIATED HIGHLY DIASTEREOSELECTIVE CONJUGATE ADDITION OF GRIGNARD-REAGENTS TO 2-SILYLOXYCYCLOPENTENECARBOXYLATES, Tetrahedron letters, 37(35), 1996, pp. 6323-6326
Citations number
22
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
37
Issue
35
Year of publication
1996
Pages
6323 - 6326
Database
ISI
SICI code
0040-4039(1996)37:35<6323:CMHDCA>2.0.ZU;2-U
Abstract
The conjugate addition of magnesium cuprates to 2-silyloxycyclopentene carboxylates leads, after desilylation, to 5-substituted-2-hydroxycycl opentanecarboxylates in high yields and diastereoselectivities. The 2- silyloxy derivatives avoid the formation of the SN2' reaction by-produ cts. No loss of selectivity is also observed when a catalytic amount o f cuprous salt is used. Copyright (C) 1996 Published by Elsevier Scien ce Ltd