Asymmetric Bronsted acid catalyzed isoindoline synthesis: Enhancement of enantiomeric ratio by stereoablative kinetic resolution

被引：208

作者：

Enders, Dieter ^{[1
]}

Narine, Arun A. ^{[1
]}

Toulgoat, Fabien ^{[1
]}

Bisschops, Tom ^{[1
]}

机构：

[1] Univ Aachen, Rhein Westfal TH Aachen, Inst Organ Chem, D-52074 Aachen, Germany

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2008年 / 47卷 / 30期

关键词：

asymmetric catalysis; aza-Michael addition; chiral Bronsted acids; Friedel-Crafts reaction; organocatalysis;

D O I：

10.1002/anie.200801354

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

(Chemical Equation Presented) Improving with time: The first catalytic asymmetric synthesis of chiral 1,3-disubstituted isoindolines is based on a Brønsted acid catalyzed one-pot reaction consisting of a Friedel-Crafts reaction and a base-catalyzed aza-Michael addition (see scheme). The enantiomeric ratio of the product significantly increases with reaction time as a result of a Brønsted acid catalyzed stereoablative kinetic resolution, which occurs in tandem to the first step. © 2008 Wiley-VCH Verlag GmbH & Co. KGaA.

引用

页码：5661 / 5665

页数：5

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