Asymmetric Synthesis of Pyrroloindolones by N-Heterocyclic Carbene Catalyzed [2+3] Annulation of α-Chloroaldehydes with Nitrovinylindoles

被引：112

作者：

Ni, Qijian ^{[1
]}

Zhang, Huan ^{[2
]}

Grossmann, Andre ^{[1
]}

Loh, Charles C. J. ^{[1
]}

Merkens, Carina ^{[3
]}

Enders, Dieter ^{[1
]}

机构：

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

[2] Nara Inst Sci & Technol NAIST, Nara 6300192, Japan

[3] Rhein Westfal TH Aachen, Inst Anorgan Chem, D-52074 Aachen, Germany

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2013年 / 52卷 / 51期

关键词：

annulation; asymmetric synthesis; indole derivatives; N-heterocyclic carbenes; organocatalysis; DIELS-ALDER REACTIONS; HIGHLY ENANTIOSELECTIVE SYNTHESIS; ALPHA; BETA-UNSATURATED ALDEHYDES; 4+2 CYCLOADDITION; STETTER REACTION; COMPUTATIONAL PREDICTIONS; STEREOSELECTIVE-SYNTHESIS; OXIDATIVE ESTERIFICATION; GAMMA-BUTYROLACTONES; ENOLATE EQUIVALENTS;

D O I：

10.1002/anie.201305957

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

NHC-enolate plus 3: N-heterocyclic carbenes (NHCs) serve as organocatalysts for the [2+3] annulation of nitrovinylindoles with α-chloroaldehydes via an intermediate azolium enolate. The method provides trans-disubstituted pyrroloindolones with good yields and excellent diastereo- and enantioselectivities. Further transformations lead to tetracyclic pyrrolo[1,2-a]indoles with potential psychotropic and other bioactivities. Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

引用

页码：13562 / 13566

页数：5

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