Highly enantioselective Diels-Alder reaction of a photochemically generated o-quinodimethane with olefins

被引：82

作者：

Grosch, B

Orlebar, CN

Herdtweck, E

Massa, W

Bach, T ^{[1
]}

机构：

[1] Tech Univ Munich, Lehrstuhl Organ Chem 1, Lichtenbergstr 4, D-85747 Garching, Germany

[2] Univ Oxford, Inorgan Chem Lab, Oxford OX1 3QR, England

[3] Tech Univ Munich, Lehrstuhl Anorgan Chem, Munich, Germany

[4] Univ Marburg, Fachbereich Chem, D-35032 Marburg, Germany

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2003年 / 42卷 / 31期

关键词：

asymmetric synthesis; Diels-Alder reaction; enantioselectivity; enols; photochemistry;

D O I：

10.1002/anie.200351567

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Four stereogenic centers in one step are established with almost perfect control of the absolute and relative configuration in a photochemically induced Diels-Alder reaction of substrate 1 and dimethyl fumarate. The carrier of the chiral information, lactam 2, fixes the substrate by hydrogen bonds in a chiral environment and in this way controls the configuration of the stereogenic centers of product 3.

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页码：3693 / 3696

页数：4

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