Synthesis of acetylenedicarboxylic acid esters and asymmetric Diels-Alder reactions of the bis (methyl (S)-lactyl) ester

…, G Chee, H McColeman

Index: Charlton, James L.; Chee, Gaiklean; McColeman, Heather Canadian Journal of Chemistry, 1995 , vol. 73, # 9 p. 1454 - 1462

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Citation Number: 23

Abstract

A general method has been developed for the preparation of acetylenedicarboxylic acid esters and applied to the synthesis of both achiral and chiral esters. Diels-Alder reactions of one of the chiral esters, the bis (methyl (S)-lactyl) ester, with various types of dienes, such as phenylbutadiene, orthoquinodimethanes, and isobenzofuran, have been investigated. Moderate asymmetric induction was observed in reactions with dienes bearing an α- ...

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