Synthesis of Cyclopropane Spirooxindoles by means of a Vinylogous Organocatalytic Cascade

被引：31

作者：

Cesar da Silva, Rodrigo ^{[1
,2
]}

Chatterjee, Indranil ^{[1
]}

Escudero-Adan, Eduardo ^{[1
]}

Weber Paixao, Marcio ^{[2
]}

Melchiorre, Paolo ^{[1
,3
]}

机构：

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

[2] Univ Fed Sao Carlos, Dept Quim, BR-97105900 Sao Carlos, SP, Brazil

[3] ICREA Inst Catalana Recerca i Estudis Avancats, Barcelona 08010, Spain

来源：

ASIAN JOURNAL OF ORGANIC CHEMISTRY | 2014年 / 3卷 / 04期

基金：

巴西圣保罗研究基金会; 欧洲研究理事会;

关键词：

alkenes; cascade reactions; iminium ions; organocatalysis; spiro compounds; DOMINO REACTIONS; ORGANOCASCADE CATALYSIS; SPIROCYCLIC OXINDOLES; STEREOCENTERS; ALDEHYDES; CONSTRUCTION; 2,4-DIENALS; 1,6-ADDITION; ACTIVATION; STRATEGIES;

D O I：

10.1002/ajoc.201400014

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The stereoselective construction of spirooxindolic cyclopropane derivatives is achieved by means of a vinylogous cascade reaction that successfully integrates a vinylogous iminium ion/dienamine tandem sequence. The chemistry capitalizes upon a rare example of asymmetric 1,6-addition to 2,4-dienals, which proceeds with exclusive -site selectivity.

引用

页码：466 / 469

页数：4