Iridium-Catalyzed Enantioselective Hydroalkynylation of Enamides for the Synthesis of Homopropargyl Amides

被引：83
作者：
Bai, Xiao-Yan [1 ]
Wang, Zi-Xuan [1 ]
Li, Bi-Jie [1 ]
机构：
[1] Tsinghua Univ, Ctr Basic Mol Sci, Dept Chem, Beijing 100084, Peoples R China
来源：
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2016年 / 55卷 / 31期
基金：
中国国家自然科学基金;
关键词：
alkynes; asymmetric catalysis; iridium; ligand design; synthetic methods; ASYMMETRIC CONJUGATE ALKYNYLATION; C-H BONDS; TERMINAL ALKYNES; CARBONYL-COMPOUNDS; STEREOSELECTIVE-SYNTHESIS; PROPARGYLATION; SILYLACETYLENES; 1,3-DIENES; EFFICIENT; CONSTRUCTION;
D O I：
10.1002/anie.201601792
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
Reported is an iridium-catalyzed asymmetric hydroalkynylation of enamides with terminal alkynes. The reaction occurs regioselectively at the beta-position of an enamide to produce homopropargyl amides. Good to high enantioselectivity was observed with an iridium complex ligated by a chiral bis(phosphine) ligand. This method provides a straightforward route to synthesize chiral homopropargyl amides with a stereocenter beta to the amide.
引用
收藏
页码：9007 / 9011
页数：5
相关论文
共 77 条
  • [1] [Anonymous], 2012, ANGEW CHEM
  • [2] [Anonymous], 2012, ANGEW CHEM
  • [3] BOWER JF, 2008, ANGEW CHEM, V121, P36
  • [4] Catalytic Carbonyl Addition through Transfer Hydrogenation: A Departure from Preformed Organometallic Reagents
    Bower, John F.
    Kim, In Su
    Patman, Ryan L.
    Krische, Michael J.
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (01) : 34 - 46
  • [5] Synthesis of Enantioenriched Homopropargylic Sulfonamides by a Three Component Reaction of Aldehydes, Sulfonamides, and Chiral Allenylsilanes
    Brawn, Ryan A.
    Panek, James S.
    [J]. ORGANIC LETTERS, 2009, 11 (19) : 4362 - 4365
  • [6] Branch-Selective Alkene Hydroarylation by Cooperative Destabilization: Iridium-Catalyzed ortho-Alkylation of Acetanilides
    Crisenza, Giacomo E. M.
    Sokolova, Olga O.
    Bower, John F.
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (49) : 14866 - 14870
  • [7] Branch-Selective Alkene Hydroarylation by Cooperative Destabilization: Iridium-Catalyzed ortho-Alkylation of Acetanilides
    Crisenza, Giacomo E. M.
    Sokolova, Olga O.
    Bower, John F.
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (49) : 14866 - 14870
  • [8] Cui L., 2010, ANGEW CHEM, V122, P9364
  • [9] A Modular, Efficient, and Stereoselective Synthesis of Substituted Piperidin-4-ols
    Cui, Li
    Li, Chaoqun
    Zhang, Liming
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2010, 49 (48) : 9178 - 9181
  • [10] Diastereoselective Synthesis of Enantiopure Homopropargylic N-tert-Butylsulfinylamines
    Cyklinsky, Mathieu
    Botuha, Candice
    Chemla, Fabrice
    Ferreira, Franck
    Perez-Luna, Alejandro
    [J]. SYNLETT, 2011, (18) : 2681 - 2684
12345678