Tetrahedron letters

Preparation and decarboxylative rearrangement of (Z)-enyne esters

JCS Woo, SD Walker, MM Faul

Index: Woo, Jacqueline C.S.; Walker, Shawn D.; Faul, Margaret M. Tetrahedron Letters, 2007 , vol. 48, # 32 p. 5679 - 5682

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Citation Number: 8

Abstract

We report herein an interesting dichotomy observed during the alkaline hydrolyses of (Z)-enyne esters of general structure 1. At room temperature, hydrolyses proceed as expected to afford enyne acids 2. However, when the reactions are carried out at elevated temperatures, the major products obtained are enones 3, the overall result of decarboxylative rearrangement (Scheme 1). We report herein the scope and mechanistic details of this enyne rearrangement ...