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

被引：131
|
作者：
Ikeda, Masahiro [1 ]
Miyake, Yoshihiro [1 ]
Nishibayashi, Yoshiaki [1 ]
机构：
[1] Univ Tokyo, Sch Engn, Inst Engn Innovat, Bunkyo Ku, Tokyo 1138656, Japan
来源：
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2010年 / 49卷 / 40期
关键词：
alkynes; homogeneous catalysis; organocatalysis; ruthenium; synthetic methods; ASYMMETRIC REDUCTIVE AMINATION; BOND-FORMING REACTIONS; ACID BINARY-SYSTEM; SUBSTITUTION-REACTIONS; BRONSTED ACID; ALPHA-ALKYLATION; RELAY CATALYSIS; ALLENYLIDENE; SEQUENCE; ALKYNYLATION;
D O I：
10.1002/anie.201002591
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
Working together: The title reaction proceeds in the presence ofa thiolate-bridged diruthenium complex (2) and a secondary amine (1) to give the corresponding propargylic alkylated products in excellent yields as a mixture of two diastereoisomers, each with high enantioselectivity. The two catalysts activate propargylic alcohols and aldehydes, respectively, and cooperatively promote the enantioselec-tive reaction. © 2010 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.
引用
收藏
页码：7289 / 7293
页数：5
相关论文
共 35 条
  • [1] Cooperative Catalytic Reactions Using Organocatalysts and Transition Metal Catalysts: Enantioselective Propargylic Alkylation of Propargylic Esters with Aldehydes
    Yoshida, Akiko
    Ikeda, Masahiro
    Hattori, Gaku
    Miyake, Yoshihiro
    Nishibayashi, Yoshiaki
    [J]. ORGANIC LETTERS, 2011, 13 (04) : 592 - 595
  • [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] Transition-Metal-Catalyzed Enantioselective Propargylic Substitution Reactions of Propargylic Alcohol Derivatives with Nucleophiles
    Nishibayashi, Yoshiaki
    [J]. SYNTHESIS-STUTTGART, 2012, 44 (04): : 489 - 503
  • [7] Development of Asymmetric Propargylic Substitution Reactions Using Transition Metal Catalysts
    Nishibayashi, Yoshiaki
    [J]. CHEMISTRY LETTERS, 2021, 50 (06) : 1282 - 1288
  • [8] AMINATION OF ALLYLIC AND PROPARGYLIC ALCOHOLS WITH DO TRANSITION-METAL IMIDO COMPLEXES
    CHAN, DMT
    [J]. ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1984, 187 (APR): : 225 - INOR
  • [9] ALLENE FORMATION VIA PROPARGYLIC HALIDES AND GRIGNARD-REAGENTS IN PRESENCE OF TRANSITION-METAL CATALYSTS
    PASTO, DJ
    HENNION, GF
    SHULTS, RH
    WATERHOUSE, A
    CHOU, SK
    [J]. ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1977, 173 (MAR20): : 43 - 43
  • [10] Direct Regiospecific and Highly Enantioselective Intermolecular a-Allylic Alkylation of Aldehydes by a Combination of Transition-Metal and Chiral Amine Catalysts
    Afewerki, Samson
    Ibrahem, Ismail
    Rydfjord, Jonas
    Breistein, Palle
    Cordova, Armando
    [J]. CHEMISTRY-A EUROPEAN JOURNAL, 2012, 18 (10) : 2972 - 2977
1234