Highly Enantioselective Michael Addition of 2-Oxindole-3-carboxylate Esters to Nitroolefins Promoted by Cinchona Alkaloid-Thiourea-Bronsted Acid Cocatalysts

被引：39

作者：

Chen, Xianjie ^{[1
,2
,3
]}

Zhu, Wei ^{[3
]}

Qian, Wangke ^{[3
]}

Feng, Enguang ^{[3
]}

Zhou, Yu ^{[3
]}

Wang, Jinfang ^{[3
]}

Jiang, Hualiang ^{[1
,2
,3
]}

Yao, Zhu-Jun ^{[1
,2
]}

Liu, Hong ^{[3
]}

机构：

[1] Nanjing Univ, Sch Chem & Chem Engn, State Key Lab Coordinat Chem, Nanjing 210093, Jiangsu, Peoples R China

[2] Nanjing Univ, Nanjing Natl Lab Microstruct, Nanjing 210093, Jiangsu, Peoples R China

[3] Chinese Acad Sci, Shanghai Inst Mat Med, State Key Lab Drug Res, Shanghai Inst Biol Sci, Shanghai 200031, Peoples R China

来源：

ADVANCED SYNTHESIS & CATALYSIS | 2012年 / 354卷 / 11-12期

基金：

中国国家自然科学基金;

关键词：

nitroolefins; 2-oxindole-3-carboxylate esters; spirooxindoles; thiourea-Bronsted cocatalysis; ASYMMETRIC MICHAEL; 1,3-DICARBONYL COMPOUNDS; CONJUGATE ADDITION; 3,3'-DISUBSTITUTED OXINDOLES; QUATERNARY STEREOCENTERS; 3-SUBSTITUTED OXINDOLES; SPIROCYCLIC OXINDOLES; CONCISE SYNTHESIS; CONSTRUCTION; CATALYSIS;

D O I：

10.1002/adsc.201200206

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

A highly efficient organocatalyzed Michael addition of 2-oxindole-3-carboxylate esters to nitroolefins using a Cinchona alkaloid-thiourea and an achiral Bronsted acid as cooperative organocatalysts is reproted that affords significantly improved enantioselectivity and diastereoselectivity. It also provides an efficient approach to the synthesis of spirooxindole derivatives with high enantioselectivity.

引用

页码：2151 / 2156

页数：6

共 56 条

[51] Paraherquamides, brevianamides, and asperparalines: Laboratory synthesis and biosynthesis. An interim report [J].

Williams, RM ;

Cox, RJ .

ACCOUNTS OF CHEMICAL RESEARCH, 2003, 36 (02) :127-139

[52] STUDIES WITH ANTIINFLAMMATORY OXINDOLECARBOXANILIDES [J].

WISEMAN, EH ;

CHIAINI, J ;

MCMANUS, JM .

JOURNAL OF MEDICINAL CHEMISTRY, 1973, 16 (02) :131-134

[53] Highly enantioselective Michael addition of 2-oxindoles to vinyl selenone in RTILs catalyzed by a Cinchona alkaloid-based thiourea [J].

Zhang, Tao ;

Cheng, Liang ;

Hameed, Shahid ;

Liu, Li ;

Wang, Dong ;

Chen, Yong-Jun .

CHEMICAL COMMUNICATIONS, 2011, 47 (23) :6644-6646

[54] Cooperative Thiourea-Bronsted Acid Organocatalysis: Enantioselective Cyanosilylation of Aldehydes with TMSCN [J].

Zhang, Zhiguo ;

Lippert, Katharina M. ;

Hausmann, Heike ;

Kotke, Mike ;

Schreiner, Peter R. .

JOURNAL OF ORGANIC CHEMISTRY, 2011, 76 (23) :9764-9776

[55] Highly Enantioselective Catalytic Benzoyloxylation of 3-Aryloxindoles Using Chiral VAPOL Calcium Phosphate [J].

Zhang, Zuhui ;

Zheng, Wenhua ;

Antilla, Jon C. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (05) :1135-1138

[56] Stereocontrolled Creation of All-Carbon Quaternary Stereocenters by Organocatalytic Conjugate Addition of Oxindoles to Vinyl Sulfone [J].

Zhu, Qiang ;

Lu, Yixin .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2010, 49 (42) :7753-7756

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