Cooperative Catalytic Reactions Using Organocatalysts and Transition Metal Catalysts: Enantioselective Propargylic Alkylation of Propargylic Esters with Aldehydes

被引:70
|
作者
Yoshida, Akiko [1 ]
Ikeda, Masahiro [1 ]
Hattori, Gaku [1 ]
Miyake, Yoshihiro [1 ]
Nishibayashi, Yoshiaki [1 ]
机构
[1] Univ Tokyo, Sch Engn, Inst Engn Innovat, Bunkyo Ku, Tokyo 1138656, Japan
关键词
ASYMMETRIC REDUCTIVE AMINATION; BOND-FORMING HYDROGENATION; ACID BINARY-SYSTEM; BRONSTED ACID; SUBSTITUTION-REACTIONS; ALPHA-ALKYLATION; MICHAEL ADDITION; ALLENYLIDENE COMPLEXES; ALLYLIC ALKYLATION; RELAY CATALYSIS;
D O I
10.1021/ol1027865
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The enantioselective propargylic alkylation of propargylic esters with aldehydes in the presence of a copper complex and an optically active secondary amine as cocatalysts has been found to give the corresponding propargylic alkylated products in good yields as a mixture of two diastereoisomers with a high enantioselectivity.
引用
收藏
页码:592 / 595
页数:4
相关论文
共 50 条
  • [1] Cooperative Catalytic Reactions Using Organocatalysts and Transition-Metal Catalysts: Enantioselective Propargylic Alkylation of Propargylic Alcohols with Aldehydes
    Ikeda, Masahiro
    Miyake, Yoshihiro
    Nishibayashi, Yoshiaki
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2010, 49 (40) : 7289 - 7293
  • [2] Cooperative Catalytic Reactions Using Organocatalysts and Transition Metal Catalysts: Propargylic Allylation of Propargylic Alcohols with α,β-Unsaturated Aldehydes
    Ikeda, Masahiro
    Miyake, Yoshihiro
    Nishibayashi, Yoshiaki
    [J]. ORGANOMETALLICS, 2012, 31 (09) : 3810 - 3813
  • [3] Cooperative Catalytic Reactions Using Lewis Acids and Organocatalysts: Enantioselective Propargylic Alkylation of Propargylic Alcohols Bearing an Internal Alkyne with Aldehydes
    Motoyama, Kazuki
    Ikeda, Masahiro
    Miyake, Yoshihiro
    Nishibayashi, Yoshiaki
    [J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2011, 2011 (12) : 2239 - 2246
  • [4] Cooperative Catalytic Reactions Using Distinct Transition-Metal Catalysts: Ruthenium- and Copper-Catalyzed Enantioselective Propargylic Alkylation
    Ikeda, Masahiro
    Miyake, Yoshihiro
    Nishibayashi, Yoshiaki
    [J]. CHEMISTRY-A EUROPEAN JOURNAL, 2012, 18 (11) : 3321 - 3328
  • [5] Cooperative Catalysis: Enantioselective Propargylic Alkylation of Propargylic Alcohols with Enecarbamates Using Ruthenium/Phosphoramide Hybrid Catalysts
    Senda, Yasushi
    Nakajima, Kazunari
    Nishibayashi, Yoshiaki
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (13) : 4060 - 4064
  • [6] Catalytic enantioselective allylboration of propargylic aldehydes
    Bhakta, Urmibhusan
    Sullivan, Erin
    Hall, Dennis G.
    [J]. TETRAHEDRON, 2014, 70 (03) : 678 - 683
  • [7] Enantioselective Copper-Catalyzed Decarboxylative Propargylic Alkylation of Propargylic Esters with β-Keto Acids
    Zhu, Fu-Lin
    Wang, Ya-Hui
    Zhang, De-Yang
    Hu, Xin-Hu
    Chen, Song
    Hou, Chuan-Jin
    Xu, Jie
    Hu, Xiang-Ping
    [J]. ADVANCED SYNTHESIS & CATALYSIS, 2014, 356 (14-15) : 3231 - 3236
  • [8] Transition-Metal-Catalyzed Enantioselective Propargylic Substitution Reactions of Propargylic Alcohol Derivatives with Nucleophiles
    Nishibayashi, Yoshiaki
    [J]. SYNTHESIS-STUTTGART, 2012, 44 (04): : 489 - 503
  • [9] Development of Asymmetric Propargylic Substitution Reactions Using Transition Metal Catalysts
    Nishibayashi, Yoshiaki
    [J]. CHEMISTRY LETTERS, 2021, 50 (06) : 1282 - 1288
  • [10] Catalytic, enantioselective alkylation of α-imino esters using late transition metal phosphine complexes as catalysts
    Ferraris, D
    Young, B
    Dudding, T
    Lectka, T
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (18) : 4548 - 4549