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

被引:17
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 67 条
  • [1] Enantioselective copper-catalyzed conjugate addition and allylic substitution reactions
    Alexakis, A.
    Backvall, J. E.
    Krause, N.
    Pamies, O.
    Dieguez, M.
    [J]. CHEMICAL REVIEWS, 2008, 108 (08) : 2796 - 2823
  • [2] [Anonymous], 2011, ANGEW CHEM
  • [3] [Anonymous], 2008, ANGEW CHEM
  • [4] [Anonymous], 2006, ANGEW CHEM
  • [5] 1,4-ADDITION OF GRIGNARD-REAGENTS AND 1,6-ADDITION OF LITHIUM ORGANOCUPRATES TO N,N-DIETHYLSORBAMIDE
    BARBOT, F
    KADIBELBAN, A
    MIGINIAC, P
    [J]. TETRAHEDRON LETTERS, 1983, 24 (46) : 5089 - 5090
  • [6] Organocatalytic asymmetric Friedel-Crafts alkylation of indoles with simple α,β-unsaturated ketones
    Bartoli, Giuseppe
    Bosco, Marcella
    Carlone, Armando
    Pesciaioli, Fabio
    Sambri, Letizia
    Melchiorre, Paolo
    [J]. ORGANIC LETTERS, 2007, 9 (07) : 1403 - 1405
  • [7] The first Suzuki cross-couplings of aryltrimethylammonium salts
    Blakey, SB
    MacMillan, DWC
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (20) : 6046 - 6047
  • [8] Asymmetric Malonic and Acetoacetic Acid Syntheses - A Century of Enantioselective Decarboxylative Protonations
    Blanchet, Jerome
    Baudoux, Jerome
    Amere, Mukkanti
    Lasne, Marie-Claire
    Rouden, Jacques
    [J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2008, 2008 (33) : 5493 - 5506
  • [9] BICYCLOIONONES + TRICYCLOIONONES
    BUCHI, G
    PERRY, CW
    KOLLER, E
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1964, 86 (24) : 5646 - &
  • [10] Cai Q., 2011, Angewandte Chemie, V123, P8824