A new synthesis of α-fluorovinylsulfones utilizing the Peterson olefination methodology
2003; Elsevier BV; Volume: 124; Issue: 1 Linguagem: Inglês
10.1016/s0022-1139(03)00194-5
ISSN1873-3328
AutoresNoriaki Asakura, Yoshinosuke Usuki, Hideo Iio,
Tópico(s)Synthetic Organic Chemistry Methods
Resumoα-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 from fluoromethyl phenyl sulfone in tetrahydrofuran (THF) also proceeds smoothly, particularly with aldehydes.
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