Mechanism of formation of. ALPHA.,. BETA.-unsaturated esters in the reaction of ethyl mercaptoacetate dianion with carbonyl compounds.

S Matsui

Index: Matsui, Syuichi Bulletin of the Chemical Society of Japan, 1984 , vol. 57, # 2 p. 426 - 434

Full Text: HTML

Citation Number: 21

Abstract

Dianion derived from ethyl mercaptoacetate undergoes aldol type reaction with a carbonyl compound to give an adduct, which exhibited low diastereoselectivity. However, the adducts obtained by the reaction with a variety of aldehydes were subsequently treated with ethyl chloroformate in the presence of trivalent phosphorus compound to give (E)-isomers of α, β- unsaturated esters in high yields with greater than 85% stereoselectivity regardless of the ...