Author:
Charlton James L.,Chee Gaiklean,McColeman Heather
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-hydroxyl group. In one case, an unusual solvent-induced reversal of asymmetric induction was observed. Keywords: acetylenedicarboxylic acid esters, phenylbutadiene, orthoquinodimethanes, isobenzofurans, Diels–Alder, asymmetric.
Publisher
Canadian Science Publishing
Subject
Organic Chemistry,General Chemistry,Catalysis
Cited by
14 articles.
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