Copper (I) mediated highly diastereoselective conjugate addition of Grignard reagents to functionalised 6-membered ring cycloalkenols. Synthesis of cyclohexanes derivatives substituted on three contiguous atoms.

Authors
Dambrin, V Villieras, M Lebreton, J Toupet, L Amri, H Villieras, J
Citation
V. Dambrin et al., Copper (I) mediated highly diastereoselective conjugate addition of Grignard reagents to functionalised 6-membered ring cycloalkenols. Synthesis of cyclohexanes derivatives substituted on three contiguous atoms., TETRAHEDR L, 40(5), 1999, pp. 871-874
Citations number
16
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON LETTERS
ISSN journal
00404039 → ACNP
Volume
40
Issue
5
Year of publication
1999
Pages
871 - 874
Database
ISI
SICI code
0040-4039(19990129)40:5<871:C(MHDC>2.0.ZU;2-G
Abstract
Copper catalysed conjugate addition of Grignard reagents to 2-silyloxycyclo hexene carboxylates in the presence of an excess chlorotrimethylsilane, lea ds diastereoselectively to related (anti) (Z) silylketene acetals. Subseque nt hydrolysis and desilylation afford 2-hydroxycyclohexane carboxylates in high yields and diastereoselectivities. (C) 1999 Published by Elsevier Scie nce Ltd. All rights reserved.