An Organocatalytic [3+2] Cyclisation Strategy for the Highly Enantioselective Synthesis of Spirooxindoles

被引：195

作者：

Voituriez, Arnaud ^{[1
]}

Pinto, Nathalie ^{[1
]}

Neel, Mathilde ^{[1
]}

Retailleau, Pascal ^{[1
]}

Marinetti, Angela ^{[1
]}

机构：

[1] Ctr Rech Gif, CNRS, UPR 2301, Inst Chim Subst Nat, F-91198 Gif Sur Yvette, France

来源：

CHEMISTRY-A EUROPEAN JOURNAL | 2010年 / 16卷 / 42期

关键词：

cyclization; organocatalysis; oxindoles; phosphanes; spiro compounds; CATALYTIC ASYMMETRIC-SYNTHESIS; ELECTRON-DEFICIENT OLEFINS; SPIROCYCLIC OXINDOLES; GLUTAMATE ANALOGS; PHOSPHINE; CONSTRUCTION; CYCLOADDITIONS; ALLENES; 5-METHYLENEHYDANTOINS; 2,3-BUTADIENOATES;

D O I：

10.1002/chem.201001791

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Power of P: Phosphine-promoted [3+2] annulation reactions between electron-poor allenes and 3-arylidene indolin-2-ones afford a new organocatalytic strategy for the synthesis of the spirocyclic core of oxindolic cyclopentanes (see scheme). Asymmetric variants of these reactions have been implemented by using chiral catalysts, giving very high levels of asymmetric induction. © 2010 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

引用

页码：12541 / 12544

页数：4

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