Highly Enantioselective Construction of Spiro[4H-pyran-3,3′-oxindoles] Through a Domino Knoevenagel/Michael/Cyclization Sequence Catalyzed by Cupreine

被引：275

作者：

Chen, Wen-Bing ^{[1
,2
]}

Wu, Zhi-Jun ^{[2
,3
]}

Pei, Qing-Lan ^{[1
,2
]}

Cun, Lin-Feng ^{[1
]}

Zhang, Xiao-Mei ^{[1
]}

Yuan, Wei-Cheng ^{[1
]}

机构：

[1] Chinese Acad Sci, Chengdu Inst Organ Chem, Chengdu 610041, Peoples R China

[2] Chinese Acad Sci, Grad Sch, Beijing, Peoples R China

[3] Chinese Acad Sci, Chengdu Inst Biol, Chengdu 610041, Peoples R China

来源：

ORGANIC LETTERS | 2010年 / 12卷 / 14期

关键词：

ANNULATED HETEROCYCLIC-SYSTEMS; ONE-POT SYNTHESIS; SPIROCYCLIC OXINDOLES; CONJUGATE ADDITIONS; STEREOSELECTIVE-SYNTHESIS; QUATERNARY STEREOCENTERS; MULTICOMPONENT REACTIONS; TERTIARY STEREOCENTERS; EFFICIENT SYNTHESIS; CINCHONA ALKALOIDS;

D O I：

10.1021/ol1009224

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The first enantioselective organocatalytic two- and three-component reactions via a domino Knoevenagel/Michael/cyclization sequence with cupreine as catalyst have been developed. A wide range of optically active spiro[4H-pyran-3,3'-oxindoles] were obtained in excellent yields (up to 99%) with good to excellent enantioselectivities (up to 97%) from simple and readily available starting materials under mild reaction conditions. These heterocyclic spirooxindoles will provide promising candidates for chemical biology and drug discovery.

引用

页码：3132 / 3135

页数：4

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