Oxaziridine-Mediated Oxyamination of Indoles: An Approach to 3-Aminoindoles and Enantiomerically Enriched 3-Aminopyrroloindolines

被引：93

作者：

Benkovics, Tamas ^{[1
]}

Guzei, Ilia A. ^{[1
]}

Yoon, Tehshik P. ^{[1
]}

机构：

[1] Univ Wisconsin, Dept Chem, Madison, WI 53706 USA

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2010年 / 49卷 / 48期

关键词：

chiral auxiliaries; copper; indoles; oxaziridines; oxyamination; CATALYTIC ASYMMETRIC-SYNTHESIS; DERIVATIVES; CYCLIZATION; TRYPTOPHAN; ALKALOIDS; 5-N-ACETYLARDEEMIN; AMINOHYDROXYLATION; PHYSOSTIGMINE; CONSTRUCTION; AMAUROMINE;

D O I：

10.1002/anie.201004635

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A radical solution: A highly regioselective copper(II)-catalyzed oxyamination of N-acyl indoles with oxaziridines gave aminal products that could be converted in a single step into 3-aminoindoles and 3-aminopyrroloindolines (see scheme). When a chiral N-acyl group was used, the core fragment of some architecturally fascinating pyrroloindoline alkaloids was formed with 91% ee. Bs=benzenesulfonyl, Moc=methoxycarbonyl. Copyright © 2010 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

引用

页码：9153 / 9157

页数：5

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