Enantioselective Michael addition of dicyanoolefins to α,β-unsaturated aldehydes in aqueous medium

被引：47
|
作者：
Lu, Jun [1 ]
Liu, Feng [1 ]
Loh, Teck-Peng [1 ]
机构：
[1] Nanyang Technol Univ, Div Chem & Biol Chem, Sch Phys & Math Sci, Singapore 637371, Singapore
来源：
ADVANCED SYNTHESIS & CATALYSIS | 2008年 / 350卷 / 11-12期
关键词：
dicyanoolefins; enantioselective Michael addition; organocatalysts; unsaturated aldehydes; water;
D O I：
10.1002/adsc.200800145
中图分类号：
O69 [应用化学];
学科分类号：
081704 ;
摘要：
A pool of water-compatible catalysts, namely dialkyl-(S)-prolinols, has been developed for the enantioselective direct vinylogous Michael addition reaction of vinylmalononitriles to alpha,beta-unsaturated aldehydes in aqueous medium. In many cases, the products can be obtained in almost optically pure form (> 96% ee) after a single recrystallization.
引用
收藏
页码：1781 / 1784
页数：4
相关论文
共 50 条
  • [1] Organocatalytic and direct asymmetric vinylogous Michael addition of α,α-dicyanoolefins to α,β-unsaturated aldehydes
    Xie, JW
    Yue, L
    Xue, D
    Ma, XL
    Chen, YC
    Wu, Y
    Zhu, J
    Deng, JG
    CHEMICAL COMMUNICATIONS, 2006, (14) : 1563 - 1565
  • [2] Enantioselective organocatalytic Michael addition of isorhodanines to α,β-unsaturated aldehydes
    Wu, Shanchao
    Li, Yu
    Zhang, Yongqiang
    Fang, Kun
    Dong, Guoqiang
    Liu, Na
    Miao, Zhenyuan
    Yao, Jianzhong
    Wang, Wei
    Zhang, Wannian
    Sheng, Chunquan
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2016, 14 (16) : 3926 - 3933
  • [3] Highly enantioselective and recyclable organocatalytic Michael addition of malonates to α,β-unsaturated aldehydes in aqueous media
    Ghosh, Subrata K.
    Dhungana, Kritanjali
    Headley, Allan D.
    Ni, Bukuo
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2012, 10 (41) : 8322 - 8325
  • [4] Organocatalytic enantioselective Michael addition reactions of fluoromalonates with α,β-unsaturated aldehydes
    LI Hao1
    2 Department of Pharmaceutical Sciences
    Science China(Chemistry), 2010, (01) : 135 - 139
  • [5] Organocatalytic enantioselective Michael addition reactions of fluoromalonates with α,β-unsaturated aldehydes
    Li Hao
    Ji YaFei
    Li Jian
    Zhang ShiLei
    Yu ChenGuang
    Wang Wei
    SCIENCE CHINA-CHEMISTRY, 2010, 53 (01) : 135 - 139
  • [6] Organocatalytic enantioselective Michael addition reactions of fluoromalonates with α,β-unsaturated aldehydes
    Hao Li
    YaFei Ji
    Jian Li
    ShiLei Zhang
    ChenGuang Yu
    Wei Wang
    Science China Chemistry, 2010, 53 : 135 - 139
  • [7] Organocatalytic enantioselective Michael addition reactions of fluoromalonates with α,β-unsaturated aldehydes
    LI HaoJI YaFeiLI JianZHANG ShiLeiYU ChenGuang WANG Wei Department of Chemistry and Chemical BiologyUniversity of New MexicoAlbuquerqueNM USA Department of Pharmaceutical SciencesSchool of PharmacyEast China University of Science and TechnologyShanghai China
    Science China(Chemistry), 2010, 53 (01) : 135 - 139
  • [8] Enantioselective organocatalytic Michael addition of malonates to α,β-unsaturated aldehydes in water
    Ma, Anqi
    Zhu, Shaolin
    Ma, Dawei
    TETRAHEDRON LETTERS, 2008, 49 (19) : 3075 - 3077
  • [9] An efficient enantioselective method for asymmetiric Michael addition of nitroalkanes to α,β-unsaturated aldehydes
    Wang, Yongcan
    Li, Pengfei
    Liang, Xinmiao
    Zhang, Tony Y.
    Ye, Jinxing
    CHEMICAL COMMUNICATIONS, 2008, (10) : 1232 - 1234
  • [10] Organocatalytic Enantioselective Decarboxylative Michael Addition of β-Keto Acids to Dicyanoolefins and Disulfonylolefins
    Wei, Yi
    Guo, Ran
    Dang, Yanfeng
    Nie, Jing
    Ma, Jun-An
    ADVANCED SYNTHESIS & CATALYSIS, 2016, 358 (17) : 2721 - 2726
12345