Metal-Free Synthesis of 3,3-Disubstituted Oxoindoles by Iodine(III)-Catalyzed Bromocarbocyclizations

被引：121

作者：

Fabry, David C. ^{[1
]}

Stodulski, Maciej ^{[1
]}

Hoerner, Stefanie ^{[1
]}

Gulder, Tanja ^{[1
]}

机构：

[1] Rhein Westfal TH Aachen, Inst Organ Chem, D-52056 Aachen, Germany

来源：

CHEMISTRY-A EUROPEAN JOURNAL | 2012年 / 18卷 / 35期

关键词：

bromocarbocyclization; heterocycles; natural products; organocatalysis; oxoindoles; CATALYTIC ASYMMETRIC-SYNTHESIS; HYPERVALENT IODINE REAGENTS; ENANTIOSELECTIVE HALOCYCLIZATION; NUCLEOPHILIC ORGANOCATALYSTS; ELECTROPHILIC BROMINE; N-BROMOSUCCINIMIDE; ATOM ECONOMY; OXINDOLES; ALKENES; CHEMISTRY;

D O I：

10.1002/chem.201201232

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

I did it: An iodine(III)-mediated bromocarbocyclization was elaborated as an efficient tool for the synthesis of oxoindoles. This method is applicable to a variety of structurally different substrates, also with chemically sensitive groups, and gives access to the heterocycles in a regio- and stereoselective fashion (see scheme). The indole-2-ones obtained can be converted easily into structurally complex target compounds, such as the alkaloid physostigmine. Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

引用

页码：10834 / 10838

页数：5

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