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
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
收藏
页码:81 / 88
页数:8
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