Highly Efficient and Stereoselective Construction of Bispirooxindole Derivatives via a Three-Component 1,3-Dipolar Cycloaddition Reaction

被引：36

作者：

Xu, Qin ^{[1
,2
]}

Wang, De ^{[1
,2
]}

Wei, Yin ^{[3
]}

Shi, Min ^{[1
,2
,3
]}

机构：

[1] E China Univ Sci & Technol, Sch Chem & Mol Engn, Key Lab Adv Mat, Shanghai 200237, Peoples R China

[2] E China Univ Sci & Technol, Sch Chem & Mol Engn, Inst Fine Chem, Shanghai 200237, Peoples R China

[3] Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organometall Chem, Shanghai 200032, Peoples R China

来源：

CHEMISTRYOPEN | 2014年 / 3卷 / 03期

基金：

中国国家自然科学基金;

关键词：

azomethine ylides; bispirooxindoles; cycloaddition; stereochemistry; substituted olefins; ALPHA-AMINO-ACIDS; CATALYTIC ASYMMETRIC-SYNTHESIS; BAYLIS-HILLMAN ADDUCTS; IMINIUM ION ROUTE; ONE-POT SYNTHESIS; X=Y-ZH COMPOUNDS; AZOMETHINE YLIDES; SPIROOXINDOLE DERIVATIVES; SPIROCYCLIC OXINDOLES; DIASTEREOSELECTIVE SYNTHESIS;

D O I：

10.1002/open.201402003

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A highly regio- and stereoselective synthesis of bispirooxindoles by 1,3-dipolar cycloaddition of in situ generated azomethine ylides from isatin and proline to different electron-deficient alkenes has been developed. The synthesis affords the desired bispiro scaffold compounds in excellent yields with high regioselectivity under mild conditions. The stereochemistry was determined by single-crystal X-ray analysis.

引用

页码：93 / 98

页数：6

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