Asymmetric Mannich reactions catalyzed by cinchona alkaloid thiourea: enantioselective one-pot synthesis of novel β-amino ester derivatives

被引:38
作者
Bai, Song [1 ]
Liang, Xueping [1 ]
Song, Baoan [1 ]
Bhadury, Pinaki S. [1 ]
Hu, Deyu [1 ]
Yang, Song [1 ]
机构
[1] Guizhou Univ, State Key Lab Breeding Base Green Pesticide & Agr, Key Lab Green Pesticide & Agr Bioengn, Minist Educ, Guiyang 550025, Peoples R China
基金
中国国家自然科学基金;
关键词
AZA-HENRY REACTION; DYNAMIC KINETIC RESOLUTION; CHIRAL LEWIS-BASE; CONJUGATE ADDITION; STRECKER REACTION; N-BOC; BIFUNCTIONAL ORGANOCATALYSTS; STEREOSELECTIVE-SYNTHESIS; ACYL IMINES; KETO-ESTERS;
D O I
10.1016/j.tetasy.2011.02.029
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
An efficient one-pot synthesis of novel beta-amino ester derivatives containing a benzoxazol moiety has been developed by using cinchona alkaloid thioureas as the organocatalyst. The adducts were isolated in high enantiomeric excess and high yield. (C) 2011 Elsevier Ltd. All rights reserved.
引用
收藏
页码:518 / 523
页数:6
相关论文
共 68 条
[61]   Bifunctional-thiourea-catalyzed diastereo- and enantioselective aza-Henry reaction [J].
Xu, XN ;
Furukawa, T ;
Okino, T ;
Miyabe, H ;
Takemoto, Y .
CHEMISTRY-A EUROPEAN JOURNAL, 2006, 12 (02) :466-476
[62]   Chiral-thiourea-catalyzed direct Mannich reaction [J].
Yamaoka, Yousuke ;
Miyabe, Hideto ;
Yasui, Yoshizurm ;
Takemoto, Yoshiji .
SYNTHESIS-STUTTGART, 2007, (16) :2571-2575
[63]   Enantioselective organocatalytic Michael addition of malonate esters to nitro olefins using bifunctional cinchonine derivatives [J].
Ye, JX ;
Dixon, DJ ;
Hynes, PS .
CHEMICAL COMMUNICATIONS, 2005, (35) :4481-4483
[64]   Highly enantioselective thiourea-catalyzed nitro-Mannich reactions [J].
Yoon, TP ;
Jacobsen, EN .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (03) :466-468
[65]   Privileged chiral catalysts [J].
Yoon, TP ;
Jacobsen, EN .
SCIENCE, 2003, 299 (5613) :1691-1693
[66]   Catalysis of 3-pyrrolidinecarboxylic acid and related pyrrolidine derivatives in enantioselective anti-Mannich-type reactions: Importance of the 3-acid group on pyrrolidine for stereocontrol [J].
Zhang, Haile ;
Mitsumori, Susumu ;
Utsumi, Naoto ;
Imai, Masanori ;
Garcia-Delgado, Noemi ;
Mifsud, Maria ;
Albertshofer, Klaus ;
Cheong, Paul Ha-Yeon ;
Houk, K. N. ;
Tanaka, Fujie ;
Barbas, Carlos F., III .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (03) :875-886
[67]   Highly Enantio- and Diastereoselective Mannich Reactions of Glycine Schiff Bases with in situ Generated N-Boc-imines Catalyzed by a Cinchona Alkaloid Thiourea [J].
Zhang, Haile ;
Syed, Salahuddin ;
Barbas, Carlos F., III .
ORGANIC LETTERS, 2010, 12 (04) :708-711
[68]   Enantioselective Three-Component Kabachnik-Fields Reaction Catalyzed by Chiral Scandium(III)-N,N′-Dioxide Complexes [J].
Zhou, Xin ;
Shang, Deju ;
Zhang, Qi ;
Lin, Lili ;
Liu, Xiaohua ;
Feng, Xiaoming .
ORGANIC LETTERS, 2009, 11 (06) :1401-1404