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
收藏
页码：93 / 98
页数：6
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