Asymmetric Addition of Indoles to Isatins Catalysed by Bifunctional Modified Cinchona Alkaloid Catalysts

被引:90
作者
Chauhan, Pankaj [1 ]
Chimni, Swapandeep Singh [1 ]
机构
[1] Guru Nanak Dev Univ, UGC Ctr Adv Studies Chem, Dept Chem, Amritsar 143005, Punjab, India
关键词
chirality; cinchona alkaloids; Friedel-Crafts reactions; organocatalysis; oxindoles; FRIEDEL-CRAFTS ALKYLATION; CONJUGATE ADDITIONS; ALDOL REACTION; ENANTIOSELECTIVE ORGANOCATALYSIS; 3-INDOLYL-3-HYDROXY OXINDOLES; CARBONYL-COMPOUNDS; ORGANIC CATALYSIS; ARYLBORONIC ACIDS; ALPHA-KETOESTERS; BOND DONORS;
D O I
10.1002/chem.201000846
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
(Figure Presented) Simple and selective: An efficient organocatalytic enantioselective method for the synthesis of substituted-3-hydroxyoxindole derivatives with a quaternary chiral carbon has been developed. The cinchona alkaloid derived catalyst catalyses the Friedel Crafts-type addition of indole derivatives to the isatin derivatives under mild conditions to provide substituted 3-hydroxyoxindoles in good to excellent yields with high enantioselectivity (see scheme). © 2010 Wiley-VCH Verlag GmbH&Co. KGaA, Weinheim.
引用
收藏
页码:7709 / 7713
页数:5
相关论文
共 83 条
[1]   Stronger bronsted acids [J].
Akiyama, Takahiko .
CHEMICAL REVIEWS, 2007, 107 (12) :5744-5758
[2]   Recent progress in chiral Bronsted acid catalysis [J].
Akiyama, Takahiko ;
Itoh, Junji ;
Fuchibe, Kohei .
ADVANCED SYNTHESIS & CATALYSIS, 2006, 348 (09) :999-1010
[3]  
[Anonymous], 2004, ANGEW CHEM-GER EDIT
[4]  
[Anonymous], 2004, Angew. Chem, V116, P5248, DOI DOI 10.1002/ANGE.200400650
[5]  
[Anonymous], 2006, ANGEW CHEM
[6]   A journey across recent advances in catalytic and stereoselective alkylation of indoles [J].
Bandini, M ;
Melloni, A ;
Tommasi, S ;
Umani-Ronchi, A .
SYNLETT, 2005, (08) :1199-1222
[7]   New catalytic approaches in the stereoselective Friedel-Crafts alkylation reaction [J].
Bandini, M ;
Melloni, A ;
Umani-Ronchi, A .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (05) :550-556
[8]  
Bandini M., 2009, Catalytic Asymmetric Friedel-Crafts Alkylations
[9]  
Bandini M., 2009, ANGEW CHEM, V121, P9786, DOI DOI 10.1002/ange.200901843
[10]   Catalytic Functionalization of Indoles in a New Dimension [J].
Bandini, Marco ;
Eichholzer, Astrid .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (51) :9608-9644