Enantioselective Organocatalytic Conjugate Addition of Alkenes to α,β-Enones

被引:15
|
作者
Cui, Lingyun [1 ]
Zhang, Long [1 ]
Luo, Sanzhong [1 ,2 ]
Cheng, Jin-Pei [1 ,2 ]
机构
[1] Chinese Acad Sci, Beijing Natl Lab Mol Sci, CAS Key Lab Mol Recognit & Funct, Inst Chem, Beijing 100190, Peoples R China
[2] Collaborat Innovat Ctr Chem Sci & Engn, Tianjin 300071, Peoples R China
基金
中国国家自然科学基金;
关键词
Synthetic methods; Organocatalysis; Conjugate addition; Enamines; Alkenes; Enantioselectivity; ALPHA; BETA-UNSATURATED CARBONYL-COMPOUNDS; CATALYZED ASYMMETRIC 1,4-ADDITION; MICHAEL ADDITION; KETONES; REAGENTS; FUNCTIONALIZATION; 1,6-ADDITION; ALKYLATION; INSERTION; OLEFINS;
D O I
10.1002/ejoc.201402353
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
We report the first example of the enantioselective conjugate addition of alkenes (aromatic enamines) to enones catalyzed by chiral primary amines. The reactions encompass a plethora of alpha,beta-enones including difficult alpha-substituted vinyl ketones to give vinylation adducts in high yields with good enantioselectivity. The methodology is of synthetic potential in accessing chiral functional materials.
引用
收藏
页码:3540 / 3545
页数:6
相关论文
共 50 条
  • [1] Organocatalytic enantioselective conjugate additions to enones
    Wang, Jian
    Li, Hao
    Zu, Liansuo
    Jiang, Wei
    Xie, Hexin
    Duan, Wenhu
    Wang, Wei
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (39) : 12652 - 12653
  • [2] Organocatalytic enantioselective conjugate additions to enones
    Wang, Jian
    Li, Hao
    Zu, Liansuo
    Jiang, Wei
    Xie, Hexin
    Duan, Wenhu
    Wang, Wei
    Journal of the American Chemical Society, 2006, 128 (39): : 12652 - 12653
  • [3] Organocatalytic Enantioselective Conjugate Addition of Azlactones to Enolizable Linear and Cyclic Enones
    Wang, Chao-Ming
    Xiao, Jun-An
    Wang, Jing
    Wang, Sha-Sha
    Deng, Zhao-Xu
    Yang, Hua
    JOURNAL OF ORGANIC CHEMISTRY, 2016, 81 (17): : 8001 - 8008
  • [4] Highly enantioselective organocatalytic conjugate addition of malonates to acyclic α,β-unsaturated enones
    Halland, N
    Aburel, PS
    Jorgensen, KA
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (06) : 661 - 665
  • [5] Enantioselective Synthesis of Functionalized Nitrocyclopropanes by Organocatalytic Conjugate Addition of Bromonitroalkanes to α,β-Unsaturated Enones
    Lv, Jian
    Zhang, Jiaming
    Lin, Zhu
    Wang, Yongmei
    CHEMISTRY-A EUROPEAN JOURNAL, 2009, 15 (04) : 972 - 979
  • [6] Organocatalytic enantioselective conjugate addition to alkynones
    Bella, M
    Jorgensen, KA
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (18) : 5672 - 5673
  • [7] Enantioselective organocatalytic amine conjugate addition
    Chen, Young K.
    Yoshida, Masanori
    MacMillan, David W. C.
    Journal of the American Chemical Society, 2006, 128 (29): : 9328 - 9329
  • [8] Enantioselective organocatalytic amine conjugate addition
    Chen, Young K.
    Yoshida, Masanori
    MacMillan, David W. C.
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (29) : 9328 - 9329
  • [9] A general organocatalytic enantioselective malonate addition to α,β-unsaturated enones
    Wascholowski, Veit
    Knudsen, Kristian Rahbek
    Mitchell, Claire E. T.
    Ley, Steven V.
    CHEMISTRY-A EUROPEAN JOURNAL, 2008, 14 (20) : 6155 - 6165
  • [10] Organocatalytic enantioselective Michael addition of thioacetic acid to enones
    Hao, L
    Zu, LS
    Wang, J
    Wang, W
    TETRAHEDRON LETTERS, 2006, 47 (18) : 3145 - 3148