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

共 43 条

[41] Construction of quaternary stereocenters by efficient and practical conjugate additions to α,β-unsaturated ketones with a chiral organic catalyst
Wu, FH
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[42] Chiral Phosphoric Acid Catalyzed Diastereo- and Enantioselective 1,4-Conjugate Addition of β-Ketoesters to Nitroolefins
Zhang, Hui
Cun, Lin-Feng
Zhang, Xiao-Mei
Yuan, Wei-Cheng
[J]. LETTERS IN ORGANIC CHEMISTRY, 2010, 7 (03) : 219 - 225
[43] A simple and clean procedure for three-component synthesis of spirooxindoles in aqueous medium
Zhu, Song-Lei
Ji, Shun-Jun
Zhang, Yong
[J]. TETRAHEDRON, 2007, 63 (38) : 9365 - 9372

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