Functionalized chiral ionic liquids as highly efficient asymmetric organocatalysts for Michael addition to nitroolefins

被引：460
作者：
Luo, Sanzhong [1 ]
Mi, Xueling
Zhang, Long
Liu, Song
Xu, Hui
Cheng, Jin-Pei
机构：
[1] Chinese Acad Sci, Inst Chem, Ctr Mol Sci, Beijing 100080, Peoples R China
[2] Nankai Univ, Dept Chem, Tianjin 300071, Peoples R China
[3] Nankai Univ, State Key Lab Elementoorgan Chem, Tianjin 300071, Peoples R China
来源：
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2006年 / 45卷 / 19期
关键词：
asymmetric catalysis; ionic liquids; Michael addition; nitroalkenes; organocatalysis;
D O I：
10.1002/anie.200600048
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
(Chemical Equation Presented) Catalytic combination: By combining the advantages of organocatalysts and ionic liquids, a functionalized chiral ionic liquid such as 1 can act as a highly efficient and reusable organocatalyst for the asymmetric Michael addition reaction of ketones and aldehydes with nitroalkenes. © 2006 Wiley-VCH Verlag GmbH & Co. KGaA.
引用
收藏
页码：3093 / 3097
页数：5
相关论文
共 80 条
[1]   Supported choline hydroxide (ionic liquid) as heterogeneous catalyst for aldol condensation reactions [J].
Abelló, S ;
Medina, F ;
Rodríguez, X ;
Cesteros, Y ;
Salagre, P ;
Sueiras, JE ;
Tichit, D ;
Coq, B .
CHEMICAL COMMUNICATIONS, 2004, (09) :1096-1097
[2]   New strategies for organic catalysis: The first highly enantioselective organocatalytic Diels-Alder reaction [J].
Ahrendt, KA ;
Borths, CJ ;
MacMillan, DWC .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (17) :4243-4244
[3]   Diamine-catalyzed asymmetric Michael additions of aldehydes and ketones to nitrostyrene [J].
Alexakis, A ;
Andrey, O .
ORGANIC LETTERS, 2002, 4 (21) :3611-3614
[4]   The use of N-alkyl-2,2′-bipyrrolidine derivatives as organocatalysts for the asymmetric Michael addition of ketones and aldehydes to nitroolefins [J].
Andrey, O ;
Alexakis, A ;
Tomassini, A ;
Bernardinelli, G .
ADVANCED SYNTHESIS & CATALYSIS, 2004, 346 (9-10) :1147-1168
[5]   Asymmetric Michael addition of α-hydroxyketones to nitroolefins catalyzed by chiral diamine [J].
Andrey, O ;
Alexakis, A ;
Bernardinelli, G .
ORGANIC LETTERS, 2003, 5 (14) :2559-2561
[6]  
[Anonymous], 2004, ANGEW CHEM, V116, P1292
[7]  
[Anonymous], 2003, ANGEW CHEM
[8]   Chiral ionic liquids, a renewal for the chemistry of chiral solvents?: Design, synthesis and applications for chiral recognition and asymmetric synthesis [J].
Baudequin, C ;
Brégeon, D ;
Levillain, J ;
Guillen, F ;
Plaquevent, JC ;
Gaumont, AC .
TETRAHEDRON-ASYMMETRY, 2005, 16 (24) :3921-3945
[9]   Ionic liquids and chirality: opportunities and challenges [J].
Baudequin, C ;
Baudoux, J ;
Levillain, J ;
Cahard, D ;
Gaumont, AC ;
Plaquevent, JC .
TETRAHEDRON-ASYMMETRY, 2003, 14 (20) :3081-3093
[10]  
Berkessel A, 2005, ASYMMETRIC ORGANOCATALYSIS: FROM BIOMIMETIC CONCEPTS TO APPLICATIONS IN ASYMMETRIC SYNTHESIS, P1, DOI 10.1002/3527604677
12345678