Stereoselective lithiation of α,β-epoxy-γ,δ-vinylsilanes and transformation into α-silylated ketones

被引：14

作者：

Courillon, C ^{[1
]}

Marié, JC ^{[1
]}

Malacria, M ^{[1
]}

机构：

[1] Univ Paris 06, CNRS, Chim Organ Lab, F-75252 Paris 05, France

来源：

TETRAHEDRON | 2003年 / 59卷 / 49期

关键词：

epoxides; ketones; regioselection; silicon and compounds;

D O I：

10.1016/j.tet.2003.10.014

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A (cis)alpha,beta-epoxy-gamma,delta-vinyl-silane undergoes lithiation alpha to the silicon atom with retention of the configuration of the oxirane. This leads to new silylated vinyloxiranes with a quaternary silylated stereogenic carbon atom. We show here the possible and efficient rearrangement of a methyl substituted adduct into a beta,gamma-unsaturated-alpha-silylated ketone. (C) 2003 Elsevier Ltd. All rights reserved.

引用

页码：9759 / 9766

页数：8

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