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

被引：461
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
    Abelló, S
    Medina, F
    Rodríguez, X
    Cesteros, Y
    Salagre, P
    Sueiras, JE
    Tichit, D
    Coq, B
    [J]. CHEMICAL COMMUNICATIONS, 2004, (09) : 1096 - 1097
  • [2] New strategies for organic catalysis: The first highly enantioselective organocatalytic Diels-Alder reaction
    Ahrendt, KA
    Borths, CJ
    MacMillan, DWC
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (17) : 4243 - 4244
  • [3] Diamine-catalyzed asymmetric Michael additions of aldehydes and ketones to nitrostyrene
    Alexakis, A
    Andrey, O
    [J]. 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
    Andrey, O
    Alexakis, A
    Tomassini, A
    Bernardinelli, G
    [J]. ADVANCED SYNTHESIS & CATALYSIS, 2004, 346 (9-10) : 1147 - 1168
  • [5] Asymmetric Michael addition of α-hydroxyketones to nitroolefins catalyzed by chiral diamine
    Andrey, O
    Alexakis, A
    Bernardinelli, G
    [J]. 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
    Baudequin, C
    Brégeon, D
    Levillain, J
    Guillen, F
    Plaquevent, JC
    Gaumont, AC
    [J]. TETRAHEDRON-ASYMMETRY, 2005, 16 (24) : 3921 - 3945
  • [9] Ionic liquids and chirality: opportunities and challenges
    Baudequin, C
    Baudoux, J
    Levillain, J
    Cahard, D
    Gaumont, AC
    Plaquevent, JC
    [J]. 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