Enantioselective Construction of Spirooxindole Derivatives: Asymmetric [3+2] Cyclization of Isothiocyanatooxindoles with Allenic Esters or 2-Butynedioic Acid Diesters

被引：57

作者：

Du, Dan ^{[1
,2
]}

Jiang, Yu ^{[1
,2
]}

Xu, Qin ^{[3
]}

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

机构：

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

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

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

来源：

ADVANCED SYNTHESIS & CATALYSIS | 2013年 / 355卷 / 11-12期

基金：

中国国家自然科学基金;

关键词：

allenic esters; asymmetric [3+2] cycloaddition; Cinchona alkaloids; organocatalysts; spirooxindole derivatives; DIELS-ALDER REACTIONS; HIGHLY EFFICIENT; CONJUGATE ADDITION; MICHAEL ADDITION; STEREOCENTERS; CATALYSIS; QUATERNARY; POTENT; SQUARAMIDES; PHOSPHINE;

D O I：

10.1002/adsc.201300460

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

A novel Cinchona alkaloid-derived organocatalyst having stronger hydrogen-bonding donors that catalyzes the asymmetric [3+2] cycloaddition of 3-isothiocyanatooxindoles with allenic esters or 2-butynedioic acid diesters has been developed, affording functionalized spirooxindole derivatives in high yields along with good to excellent enantioselectivities under mild conditions. We also found that by changing the ratio of the substrates, different spirooxindole derivatives could be obtained in high yields along with good to excellent enantioselectivities.

引用

页码：2249 / 2256

页数：8

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