Functionalised allylsilanes from silylcopper reagents and allene. A usefulstrategy for cyclopentane annulations

Authors
Barbero, A Garcia, C Pulido, FJ
Citation
A. Barbero et al., Functionalised allylsilanes from silylcopper reagents and allene. A usefulstrategy for cyclopentane annulations, TETRAHEDRON, 56(18), 2000, pp. 2739-2751
Citations number
46
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON
ISSN journal
00404020 → ACNP
Volume
56
Issue
18
Year of publication
2000
Pages
2739 - 2751
Database
ISI
SICI code
0040-4020(20000428)56:18<2739:FAFSRA>2.0.ZU;2-J
Abstract
Silylcupration of allene using phenyldimethylsilylcopper or t-butyldiphenyl silylcopper followed by reaction with alpha,beta-unsaturated acyl chlorides , aldehydes or ketones affords allylsilane-containing divinyl ketones and o xoallylsilanes, respectively. They undergo highly stereocontrolled silicon- assisted intramolecular cyclizations when treated with protic or Lewis acid leading to cyclopentane ring-formation. (C) 2000 Elsevier Science Ltd. All rights reserved.