Tetrahedron

Nucleophilic carbene-catalyzed redox-esterification reaction of α-halo-α, β-unsaturated aldehyde

XB Wang, XL Zou, GF Du, ZY Liu, B Dai

Index: Wang, Xiang-Bo; Zou, Xiao-Lei; Du, Guang-Fen; Liu, Zhi-Yong; Dai, Bin Tetrahedron, 2012 , vol. 68, # 32 p. 6498 - 6503

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Citation Number: 14

Abstract

A nucleophilic carbene catalyzed redox esterification between α-halo-α, β-unsaturated aldehydes and various alcohols has been developed. Interestingly, the reaction provided α, β-unsaturated esters instead of the saturated α-halo substituted esters as the only product in good to high yield with excellent trans-selectivity, presumably via the umpolung-halo- elimination pathway.