ASYMMETRIC DIELS-ALDER CYCLOADDITIONS WITH CHIRAL CARBAMOYL DIENOPHILES

被引：29

作者：

DEFOIN, A ^{[1
]}

BROUILLARDPOICHET, A ^{[1
]}

STREITH, J ^{[1
]}

机构：

[1] UNIV HAUTE ALSACE,ECOLE NATL SUPER CHIM MULHOUSE,3 RUE ALFRED WERNER,F-68093 MULHOUSE,FRANCE

来源：

HELVETICA CHIMICA ACTA | 1992年 / 75卷 / 01期

关键词：

D O I：

10.1002/hlca.19920750108

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Chiral acylnitroso dienophiles 14, which were obtained from L-proline and from D-mandelic acid, reacted with cyclohexa-1,3-diene to give the expected diastereoisomers 15 and 16 (Scheme 2 and Table 1). The d.e. values for these Diels-Alder reactions were moderate; they are related to the molecular stiffness of the dienophiles. The absolute configuration of the major cycloadducts was interpreted in terms of HOMO/LUMO interactions, the approach being 'endo' and the acylnitroso dienophiles reacting from their s-cis-conformation.

引用

页码：109 / 123

页数：15

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