Rhodium-Catalyzed Enantioselective Reductive Arylation: Convenient Access to 3,3-Disubstituted Oxindoles

被引：48

作者：

Jang, Young Jin ^{[1
]}

Larin, Egor M. ^{[1
]}

Lautens, Mark ^{[1
]}

机构：

[1] Univ Toronto, Dept Chem, Davenport Res Labs, Toronto, ON M5S 3H6, Canada

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2017年 / 56卷 / 39期

基金：

加拿大自然科学与工程研究理事会;

关键词：

cyclization; homogeneous catalysis; oxindoles; reductive arylation; rhodium; CARBONYLATIVE CYCLIZATION REACTIONS; ELECTRON-DEFICIENT OLEFINS; TANDEM CONJUGATE ADDITION; ASYMMETRIC 1,4-ADDITION; ALDOL REACTION; ORGANOBORON REAGENTS; STITCHING REACTION; ALPHA-ARYLATION; AQUEOUS-MEDIA; ACIDS;

D O I：

10.1002/anie.201704922

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A rhodium-Josiphos(L*) catalyzed enantioselective intramolecular hydroarylation reaction is described. The reductive cyclization of o-bromoaniline-derived acrylamides provides convenient access to 3,3-disubstituted oxindoles in good yields and with excellent enantioselectivity across a range of substrates. We propose that the key cyclization proceeds via a rhodium(III) intermediate. Overall, this method represents an unusual mode of reactivity for rhodium catalysis and is complementary to palladium(0)-catalyzed -arylation methods.

引用

页码：11927 / 11930

页数：4

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