Silylcupration of allenes followed by reaction with enones. A new strategyfor the synthesis of methylenecyclopentanols

Authors
Barbero, A Garcia, C Pulido, FJ
Citation
A. Barbero et al., Silylcupration of allenes followed by reaction with enones. A new strategyfor the synthesis of methylenecyclopentanols, TETRAHEDR L, 40(36), 1999, pp. 6649-6652
Citations number
18
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON LETTERS
ISSN journal
00404039 → ACNP
Volume
40
Issue
36
Year of publication
1999
Pages
6649 - 6652
Database
ISI
SICI code
0040-4039(19990903)40:36<6649:SOAFBR>2.0.ZU;2-B
Abstract
Silylcupration of allene using phenyldimethylsilyl-copper followed by conju gated addition to alpha,beta-unsaturated ketones affords oxoallylsilanes wi th different substitution patterns. When the former oxoallylsilanes are tre ated with a Lewis acid they undergo highly stereoselective allylsilane term inated cyclization leading to mono-, bi-, and tricyclic methylenecyclopenta nols. (C) 1999 Elsevier Science Ltd. All rights reserved.