Highly enantioselective michael addition of aromatic ketones to nitroolefins promoted by chiral bifunctional primary amine-thiourea catalysts based on saccharides

被引:230
|
作者
Liu, Kun [1 ]
Cui, Han-Feng [1 ]
Nie, Jing [1 ]
Dong, Ke-Yan [1 ]
Li, Xiao-Juan [1 ]
Ma, Jun-An [1 ]
机构
[1] Tianjin Univ, Dept Chem, Tianjin 300072, Peoples R China
关键词
D O I
10.1021/ol0701666
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A new class of thiourea catalysts have been developed which integrate saccharide and primary amine moieties into one small organic molecule. These simple catalysts are shown to be highly enantioselective for direct Michael addition of aromatic ketones to a range of nitroolefins (up to 98% ee).
引用
收藏
页码:923 / 925
页数:3
相关论文
共 50 条
  • [1] Highly enantioselective Michael addition of acetone to nitroolefins catalyzed by chiral bifunctional primary amine-thiourea catalysts with acetic acid
    Gu, Qing
    Guo, Xing-Tao
    Wu, Xin-Yan
    TETRAHEDRON, 2009, 65 (27) : 5265 - 5270
  • [2] Highly enantioselective direct conjugate addition of ketones to nitroalkenes promoted by a chiral primary amine-thiourea catalyst
    Huang, Hongbing
    Jacobsen, Eric N.
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (22) : 7170 - 7171
  • [3] Highly enantioselective direct conjugate addition of ketones to nitroalkenes promoted by a chiral primary amine-thiourea catalyst
    Huang, Hongbing
    Jacobsen, Eric N.
    Journal of the American Chemical Society, 2006, 128 (22): : 7170 - 7171
  • [4] Highly effective and enantioselective Michael addition of 4-hydroxycoumarin to α,β-unsaturated ketones promoted by simple chiral primary amine thiourea bifunctional catalysts
    Mei, Ren-Qiang
    Xu, Xiao-Ying
    Li, Yan-Chun
    Fu, Ji-Ya
    Huang, Qing-Chun
    Wang, Li-Xin
    TETRAHEDRON LETTERS, 2011, 52 (14) : 1566 - 1568
  • [5] Highly Enantioselective Biginelli Reaction Promoted by Chiral Bifunctional Primary Amine-Thiourea Catalysts: Asymmetric Synthesis of Dihydropyrimidines
    Wang, Yangyun
    Yang, Haitao
    Yu, Jiepan
    Miao, Zhiwei
    Chen, Ruyu
    ADVANCED SYNTHESIS & CATALYSIS, 2009, 351 (18) : 3057 - 3062
  • [6] Highly Enantioselective Michael Addition of Malonates to Nitroolefins Catalyzed by Chiral Bifunctional Tertiary Amine-Thioureas Based on Saccharides
    Li, Xiao-Juan
    Liu, Kun
    Ma, Hai
    Nie, Jing
    Ma, Jun-An
    SYNLETT, 2008, (20) : 3242 - 3246
  • [7] Primary amine-thiourea grafted graphene-based heterogeneous chiral catalysts for highly enantioselective Michael additions
    Badr, Sayed Mustafa
    Azlouk, Manel
    Zor, Erhan
    Bingol, Haluk
    Durmaz, Mustafa
    MOLECULAR CATALYSIS, 2022, 526
  • [8] Highly enantio- and diastereoselective Michael addition of cyclohexanone to nitroolefins catalyzed by a chiral glucose-based bifunctional secondary amine-thiourea catalyst
    Lu, Aidang
    Gao, Peng
    Wu, Yang
    Wang, Youming
    Zhou, Zhenghong
    Tang, Chuchi
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2009, 7 (15) : 3141 - 3147
  • [9] Highly enantioselective addition of ketones to nitroolefins catalyzed by new thiourea-amine bifunctional organocatalysts
    Tsogoeva, SB
    Wei, SW
    CHEMICAL COMMUNICATIONS, 2006, (13) : 1451 - 1453
  • [10] Asymmetric Michael Addition of Aromatic Ketones to Nitroolefins Catalyzed by Simple Chiral Bifunctional Primary Amine-Thioureas
    Wang, Liangliang
    Xu, Xiaoying
    Huang, Jun
    Peng, Lin
    Huang, Qingchun
    Wang, Lixin
    LETTERS IN ORGANIC CHEMISTRY, 2010, 7 (05) : 367 - 372