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

N Asakura, Y Usuki, H Iio

Index: Asakura, Noriaki; Usuki, Yoshinosuke; Iio, Hideo Journal of Fluorine Chemistry, 2003 , vol. 124, # 1 p. 81 - 88

Full Text: HTML

Citation Number: 27

Abstract

α-Fluoro-α-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 α-fluorovinylsulfones 6, in some cases with high E-stereoselectivity. One-pot reaction with 4 generated in situ ...