SYNTHESIS OF ACETYLENEDICARBOXYLIC ACID-ESTERS AND ASYMMETRIC DIELS-ALDER REACTIONS OF THE BIS(METHYL (S)-LACTYL) ESTER

被引：12

作者：

CHARLTON, JL

CHEE, G

MCCOLEMAN, H

机构：

来源：

CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE | 1995年 / 73卷 / 09期

关键词：

ACETYLENEDICARBOXYLIC ACID ESTERS; PHENYLBUTADIENE; ORTHOQUINODIMETHANES; ISOBENZOFURANS; DIELS-ALDER; ASYMMETRIC;

D O I：

10.1139/v95-180

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

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 alpha-hydroxyl group. In one case, an unusual solvent-induced reversal of asymmetric induction was observed.

引用

页码：1454 / 1462

页数：9

共 37 条

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