The Journal of organic chemistry

Enantioselective synthesis of the optically active α-methylene-β-hydroxy esters, equivalent compounds to morita-baylis-hillman adducts, using successive asymmetric …

I Shiina, Y Yamai, T Shimazaki

Index: Shiina, Isamu; Yamai, Yu-Suke; Shimazaki, Takahisa Journal of Organic Chemistry, 2005 , vol. 70, # 20 p. 8103 - 8106

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Citation Number: 14

Abstract

The asymmetric aldol reaction of a tetra-substituted ketene silyl acetal including an alkylseleno group with aldehydes has been developed by the promotion of Sn (OTf) 2 coordinated with a chiral diamine to afford the corresponding aldols having chiral quaternary centers at the α-positions. The facile oxidative deselenization of these aldol compounds produces optically active α-methylene-β-hydroxy esters which correspond to adducts ...