Catalytic Asymmetric [3+2] Annulation of Allylsilanes with Isatins: Synthesis of Spirooxindoles

被引：110

作者：

Hanhan, Nadine V. ^{[1
]}

Ball-Jones, Nicolas R. ^{[1
]}

Tran, Ngon T. ^{[1
]}

Franz, Annaliese K. ^{[1
]}

机构：

[1] Univ Calif Davis, Dept Chem, Davis, CA 95616 USA

来源：

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

关键词：

allylic compounds; annulation; asymmetric catalysis; enantioselectivity; scandium; ENANTIOSELECTIVE SYNTHESIS; RING ANNULATION; ALLYLATION; CYCLOADDITION; ADDITIONS; SILICON; ESTERS; NUCLEOPHILICITY; OXINDOLES; OXIDATION;

D O I：

10.1002/anie.201105739

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Silyl-inspired spirocycle: The title reaction is the first example of a catalytic asymmetric [3+2] annulation reaction with allylsilanes. The annulation reaction utilizes a chiral ScCl 2(SbF 6)/L catalyst and TMSCl as a promoter to afford spirooxindoles in excellent enantioselectivity at room temperature. The Si-C bond can be oxidized to deliver hydroxy-substituted spirooxindoles. TMS=trimethylsilyl. Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

引用

页码：989 / 992

页数：4

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