Enantioselective organocatalytic aldol reaction of unactivated ketones with isatins

被引：73

作者：

Allu, Suresh ^{[1
]}

Molleti, Nagaraju ^{[2
]}

Panem, Ramachandrarao ^{[1
]}

Singh, Vinod K. ^{[1
,2
]}

机构：

[1] Indian Inst Technol, Dept Chem, Kanpur 208016, Uttar Pradesh, India

[2] Indian Inst Sci Educ & Res, Dept Chem, Bhopal 462023, MP, India

来源：

TETRAHEDRON LETTERS | 2011年 / 52卷 / 32期

关键词：

Organocatalysis; Thiourea; Isatin; Enamine mechanism; 3-Alkyl-3-hydroxyindolin-2-ones; CINCHONA ALKALOID DERIVATIVES; ASYMMETRIC ALDOL; STEREOSELECTIVE-SYNTHESIS; MICHAEL ADDITION; PROLINE; ACETALDEHYDE; ACID; CONDENSATION; ENOLIZATION; ALDEHYDES;

D O I：

10.1016/j.tetlet.2011.05.013

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Enantioselective organocatalytic direct aldol reaction of unactivated ketones with various isatin derivatives was developed using cinchonine based urea ligand employing a noncovalent catalysis mechanism. Using this protocol we can access functionalized 3-alkyl-3-hydroxyindolin-2-ones in high yields with good to excellent enantioselectivities. (C) 2011 Elsevier Ltd. All rights reserved.

引用

页码：4080 / 4083

页数：4

共 52 条

[1] Water influences the enantioselectivity in the proline or prolinamide-catalyzed aldol addition of acetone to isatins [J].

Angelici, Gaetano ;

Correa, Rodrigo J. ;

Garden, Simon J. ;

Tomasini, Claudia .

TETRAHEDRON LETTERS, 2009, 50 (07) :814-817

[2]

[Anonymous], 2009, Curr. Bioact. Compd., DOI [10.2174/157340709787580900, DOI 10.2174/157340709787580900]

[3] L-proline-catalyzed asymmetric aldol condensation of N-substituted isatins with acetone [J].

Chen, Gang ;

Wang, Ye ;

He, Hongping ;

Gao, Suo ;

Yang, Xiaosheng ;

Hao, Xiaojiang .

HETEROCYCLES, 2006, 68 (11) :2327-2333

[4] Organocatalytic asymmetric aldol reaction of ketones with isatins: straightforward stereoselective synthesis of 3-alkyl-3-hydroxyindolin-2-ones [J].

Chen, Jia-Rong ;

Liu, Xiao-Peng ;

Zhu, Xiao-Yu ;

Li, Liang ;

Qiao, Yong-Feng ;

Zhang, Jian-Ming ;

Xiao, Wen-Jing .

TETRAHEDRON, 2007, 63 (42) :10437-10444

[5] Highly enantioselective aldol reaction of acetaldehyde and isatins only with 4-hydroxydiarylprolinol as catalyst: concise stereoselective synthesis of (R)-convolutamydines B and E, (-)-donaxaridine and (R)-chimonamidine [J].

Chen, Wen-Bing ;

Du, Xi-Lin ;

Cun, Lin-Feng ;

Zhang, Xiao-Mei ;

Yuan, Wei-Cheng .

TETRAHEDRON, 2010, 66 (07) :1441-1446

[6] Small-molecule H-bond donors in asymmetric catalysis [J].

Doyle, Abigail G. ;

Jacobsen, Eric N. .

CHEMICAL REVIEWS, 2007, 107 (12) :5713-5743

[7] Nucleophilic chiral amines as catalysts in asymmetric synthesis [J].

France, S ;

Guerin, DJ ;

Miller, SJ ;

Lectka, T .

CHEMICAL REVIEWS, 2003, 103 (08) :2985-3012

[8] Synthesis of Chiral Organocatalysts derived from Aziridines: Application in Asymmetric Aldol Reaction [J].

Gandhi, Shikha ;

Singh, Vinod K. .

JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (23) :9411-9416

[9] Quinidine Thiourea-Catalyzed Aldol Reaction of Unactivated Ketones: Highly Enantioselective Synthesis of 3-Alkyl-3-hydroxy-indolin-2-ones [J].

Guo, Qunsheng ;

Bhanushali, Mayur ;

Zhao, Cong-Gui .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2010, 49 (49) :9460-9464

[10] Enantioselective Aldol Reaction using Recyclable Montmorillonite-Entrapped N-(2-Thiophenesulfonyl)prolinamide [J].

Hara, Noriyuki ;

Nakamura, Shuichi ;

Shibata, Norio ;

Toru, Takeshi .

ADVANCED SYNTHESIS & CATALYSIS, 2010, 352 (10) :1621-1624

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