Dioxindole in Asymmetric Catalytic Synthesis: Routes to Enantioenriched 3-Substituted 3-Hydroxyoxindoles and the Preparation of Maremycin A

被引：184

作者：

Bergonzini, Giulia ^{[2
]}

Melchiorre, Paolo ^{[1
,2
]}

机构：

[1] ICREA Inst Catalana Recerca & Estudis Avancats, Barcelona 08010, Spain

[2] ICIQ Inst Chem Res Catalonia, Tarragona 43007, Spain

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2012年 / 51卷 / 04期

关键词：

asymmetric synthesis; molecular complexity; organocatalysis; oxindoles; spiro compounds; ENANTIOSELECTIVE SYNTHESIS; ISATIN DERIVATIVES; INDOLE DERIVATIVES; OXINDOLES; ENALS; 3-HYDROXY-2-OXINDOLES; HYDROXYLATION; NITROALKENES; ALDEHYDES; ADDITIONS;

D O I：

10.1002/anie.201107443

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Taming the reactivity: Understanding the nucleophilicity of dioxindole under different reaction conditions is key to a direct and easy access to valuable spiro oxindole Î butyrolactones and 3-substituted 3-hydroxyoxindole derivatives in excellent yields and enantioselectivities (see scheme). The preparation of maremycin A serves as an example for the potential usefulness of this previously unexplored reactivity in natural product synthesis. Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

引用

页码：971 / 974

页数：4

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