A new synthesis of α-fluorovinylsulfones utilizing the Peterson olefination methodology

被引：29

作者：

Asakura, N ^{[1
]}

Usuki, Y ^{[1
]}

Iio, I ^{[1
]}

机构：

[1] Osaka City Univ, Grad Sch Sci, Dept Mat Sci, Sumiyoshi Ku, Osaka 5588585, Japan

来源：

JOURNAL OF FLUORINE CHEMISTRY | 2003年 / 124卷 / 01期

关键词：

gamma-fluoro-alpha-silyl sulfone; Peterson olefination; monofluorinated building block;

D O I：

10.1016/S0022-1139(03)00194-5

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

alpha-Fluoro-alpha-silyl-substituted sulfones 1 are readily prepared from fluoromethyl phenyl sulfone and the appropriate silyl chloride. The use of TBSCl improves both the stability and yield of 1. Lithium derivatives 4 undergo a smooth Peterson olefination reaction with less-enolizable carbonyl compounds to give moderate to good yields of the expected alpha-fluorovinylsulfones 6, in some cases with high E-stereoselectivity. One-pot reaction with 4 generated in situ from fluoromethyl phenyl sulfone in tetrahydrofuran (THF) also proceeds smoothly, particularly with aldehydes. (C) 2003 Elsevier B.V. All rights reserved.

引用

页码：81 / 88

页数：8

共 24 条

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