Nickel-catalyzed three-component [3+2+2] cocyclization of ethyl cyclopropylideneacetate and alkynes - Selective synthesis of multisubstituted cycloheptadienes

被引:109
|
作者
Komagawa, S [1 ]
Saito, S [1 ]
机构
[1] Tokyo Univ Sci, Dept Chem, Tokyo 1628601, Japan
关键词
alkynes; cycloaddition; cycloheptadienes; nickel; synthetic methods;
D O I
10.1002/anie.200504050
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
(Chemical Equation Presented) Ménage à trois: Seven-membered carbocycles are formed by the three-component [3+2+2] cycloaddition of ethyl cyclopropylideneacetate and two different alkynes in the presence of a Ni 0/PPh3 catalyst (see scheme). In this one-pot reaction, a highly chemo- and regioselective coupling proceeds, and the cycloheptadiene derivatives are isolated as single isomers. © 2006 Wiley-VCH Verlag GmbH & Co. KGaA.
引用
收藏
页码:2446 / 2449
页数:4
相关论文
共 50 条
  • [1] Nickel-catalyzed intermolecular [3+2+2] cocyclization of ethyl cyclopropylideneacetate and alkynes
    Saito, S
    Masuda, M
    Komagawa, S
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (34) : 10540 - 10541
  • [2] Mechanistic Insight into the Nickel-Catalyzed Intermolecular [3+2+2] Cocyclization of Ethyl Cyclopropylideneacetate with Alkynes: DFT Calculations
    An, Yanhong
    Cheng, Caihong
    Pan, Ben
    Wang, Zhihong
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2012, 2012 (21) : 3911 - 3915
  • [3] Nickel-catalyzed intermolecular [3+2+2] cocyclization of ethyl cyclopropylideneacetate and alkynes. Synthesis of seven-membered carbocycles
    Saito, Shinichi
    Komagawa, Shinsuke
    Azumaya, Isao
    Masuda, Manami
    JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (24): : 9114 - 9120
  • [4] Synthesis of Vinylcycloheptadienes by the Nickel-Catalyzed Three-Component [3+2+2] Cocyclization. Application to the Synthesis of Polycyclic Compounds
    Komagawa, Shinsuke
    Takeuchi, Kouhei
    Sotome, Ikuo
    Azumaya, Isao
    Masu, Hyuma
    Yamasaki, Ryu
    Saito, Shinichi
    JOURNAL OF ORGANIC CHEMISTRY, 2009, 74 (09): : 3323 - 3329
  • [5] Nickel-Catalyzed [3+2+2] Cycloaddition of Ethyl Cyclopropylideneacetate and Heteroatom-Substituted Alkynes: Application to Selective Three-Component Reaction with 1,3-Diynes
    Yamasaki, Ryu
    Terashima, Natsuki
    Sotome, Ikuo
    Komagawa, Shunsuke
    Saito, Shinichi
    JOURNAL OF ORGANIC CHEMISTRY, 2010, 75 (02): : 480 - 483
  • [6] Ni-catalyzed [3+2+2] cycloaddition of ethyl cyclopropylideneacetate and 1,3-diynes. Application to the three-component cycloaddition
    Yamasaki, Ryu
    Sotome, Ikuo
    Komagawa, Shunsuke
    Azumaya, Isao
    Masu, Hyuma
    Saito, Shinichi
    TETRAHEDRON LETTERS, 2009, 50 (10) : 1143 - 1145
  • [7] Nickel-Catalyzed Three-Component [2+2+2] Cycloaddition Reaction of Arynes, Alkenes, and Alkynes
    Qiu, Zaozao
    Xie, Zuowei
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (31) : 5729 - 5732
  • [8] Synthesis of Vinylcycloheptadienes by the Nickel-Catalyzed Three-Component [3 + 2 + 2] Cocyclization. Application to the Synthesis of Polycyclic Compounds (vol 74, pg 3323, 2009)
    Komagawa, Shinsuke
    Takeuchi, Kouhei
    Sotome, Ikuo
    Azumaya, Isao
    Masu, Hyuma
    Yamasaki, Ryu
    Saito, Shinichi
    JOURNAL OF ORGANIC CHEMISTRY, 2009, 74 (15): : 5766 - 5766
  • [9] Nickel-Catalyzed Three-Component Cycloadditions of Enoates, Alkynes, and Aldehydes
    Jenkins, Aireal D.
    Robo, Michael T.
    Zimmerman, Paul M.
    Montgomery, John
    JOURNAL OF ORGANIC CHEMISTRY, 2020, 85 (05): : 2956 - 2965
  • [10] Nickel-catalyzed [3+2+2] cycloaddition of ethyl cyclopropylideneacetate and diynes. Synthesis of 7,6-and 7,5-fused bicyclic compounds
    Maeda, Kyotaro
    Saito, Shinichi
    TETRAHEDRON LETTERS, 2007, 48 (18) : 3173 - 3176