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
  • [21] Organocatalytic enantioselective conjugate addition of ketones to isatylidine malononitriles
    Liu, Lu
    Wu, Deyan
    Li, Xiangmin
    Wang, Sinan
    Li, Hao
    Li, Jian
    Wang, Wei
    CHEMICAL COMMUNICATIONS, 2012, 48 (11) : 1692 - 1694
  • [22] Enantioselective and Regioselective Organocatalytic Conjugate Addition of Malonates to Nitroenynes
    Li, Xiao-Jiao
    Peng, Fang-Zhi
    Li, Xiang
    Wu, Wen-Tao
    Sun, Zhong-Wen
    Li, Ying-Mei
    Zhang, Shao-Xiong
    Shao, Zhi-Hui
    CHEMISTRY-AN ASIAN JOURNAL, 2011, 6 (01) : 220 - 225
  • [23] CATALYTIC ASYMMETRIC INDUCTION IN ENANTIOSELECTIVE CONJUGATE ADDITION OF DIALKYLZINCS TO ENONES
    SOAI, K
    YOKOYAMA, S
    HAYASAKA, T
    EBIHARA, K
    JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (17): : 4148 - 4149
  • [24] Ni(II)-Catalyzed Enantioselective Conjugate Addition of Acetylenes to α,β-Enones
    Larionov, Oleg V.
    Corey, E. J.
    ORGANIC LETTERS, 2010, 12 (02) : 300 - 302
  • [25] Highly Enantioselective Organocatalytic Conjugate Addition of Nitromethane to Benzylidene Acetones
    Szanto, Gabor
    Bombicz, Petra
    Gruen, Alajos
    Kadas, Istvan
    CHIRALITY, 2008, 20 (10) : 1120 - 1126
  • [26] Enantioselective Organocatalytic Conjugate Addition of Fluorocarbon Nucleophiles to α,β-Unsaturated Aldehydes
    Ullah, Farman
    Zhao, Gui-Ling
    Deiana, Luca
    Zhu, Mingzhao
    Dziedzic, Pawel
    Ibrahem, Ismail
    Hammar, Peter
    Sun, Junliang
    Cordova, Armando
    CHEMISTRY-A EUROPEAN JOURNAL, 2009, 15 (39) : 10013 - 10017
  • [27] Enantioselective Organocatalytic Conjugate Addition of Aldehydes to α,β-Unsaturated Thiol Esters
    Zhu, Shaolin
    Wang, You
    Ma, Dawei
    ADVANCED SYNTHESIS & CATALYSIS, 2009, 351 (16) : 2563 - 2566
  • [28] First enantioselective organocatalytic conjugate addition of aldehydes to vinyl phosphonates
    Sulzer-Mosse, Sarah
    Tissot, Matthieu
    Alexakis, Alexandre
    ORGANIC LETTERS, 2007, 9 (19) : 3749 - 3752
  • [29] Enantioselective organocatalytic conjugate addition of α-nitroacetate to α,β-unsaturated ketones in water
    Moon, Hyoung Wook
    Kim, Dae Young
    TETRAHEDRON LETTERS, 2010, 51 (21) : 2906 - 2908
  • [30] Organocatalytic highly enantioselective conjugate addition of aldehydes to alkylidine malonates
    Zhao, Gui-Ling
    Vesely, Jan
    Sun, Junliang
    Christensen, Kirsten E.
    Bonneau, Charlotte
    Cordova, Armando
    ADVANCED SYNTHESIS & CATALYSIS, 2008, 350 (05) : 657 - 661