Organic letters

Mesyloxy-group migration as the stereoselective preparation method of various functionalized olefins and its reaction mechanism

T Yamazaki, S Hiraoka, J Sakamoto, T Kitazume

Index: Yamazaki, Takashi; Hiraoka, Shuichi; Sakamoto, Johei; Kitazume, Tomoya Organic Letters, 2001 , vol. 3, # 5 p. 743 - 746

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Citation Number: 13

Abstract

It was demonstrated that mesylation of appropriate γ, γ-difluorinated allylic alcohols under usual conditions furnished the corresponding α, α-difluorinated allylic mesylates, possibly by way of 1, 3-mesyloxy-group migration after formation of the expected “normal” intermediates, γ, γ-difluorinated allylic mesylates. This rearrangement was conveniently applied to the construction of trisubstituted allylic alcohols, α, β-unsaturated esters, amides, or ketones in ...