Nickel-catalyzed [3+2+2] cycloaddition of ethyl cyclopropylideneacetate and diynes. Synthesis of 7,6-and 7,5-fused bicyclic compounds

被引:49
|
作者
Maeda, Kyotaro [1 ]
Saito, Shinichi [1 ]
机构
[1] Tokyo Univ Sci, Fac Sci, Dept Chem, Shinjuku Ku, Tokyo 1628601, Japan
关键词
D O I
10.1016/j.tetlet.2007.03.051
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The [3+2+2] cycloaddition reaction of ethyl cyclopropylideneacetate (1) and diynes proceeded in the presence of Ni(0) catalysts, and bicyclic compounds were isolated in good yields. The reaction provided a new approach to 7,6- and 7,5-fused bicyclic compounds. (c) 2007 Elsevier Ltd. All rights reserved.
引用
收藏
页码:3173 / 3176
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] Efficient nickel-catalyzed [2+2+2] cycloaddition of CO2 and diynes.
    Louie, J
    Farnworth, MV
    Gibby, JE
    Tekavec, TN
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2003, 225 : U282 - U282
  • [3] 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
  • [4] PEPTIDOMIMETIC SYNTHESIS - UTILIZATION OF N-ACYLIMINIUM ION CYCLIZATION CHEMISTRY IN THE GENERATION OF 7,6-FUSED AND 7,5-FUSED BICYCLIC LACTAMS
    ROBL, JA
    TETRAHEDRON LETTERS, 1994, 35 (03) : 393 - 396
  • [5] 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
  • [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 [3+2+2] cocyclization of ethyl cyclopropylideneacetate and alkynes - Selective synthesis of multisubstituted cycloheptadienes
    Komagawa, S
    Saito, S
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (15) : 2446 - 2449
  • [8] 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
  • [9] ORGN 635-Synthesis of polycyclic cycloheptadienes by the nickel-catalyzed [3+2+2] cycloaddition and sequential [4+2] cycloaddition
    Komagawa, Shinsuke
    Takeuchi, Kouhei
    Sotome, Ikuo
    Yamasaki, Ryu
    Saito, Shinichi
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2008, 236
  • [10] Nickel-Catalyzed Intramolecular [3+2+2] Cycloadditions of Alkylidenecyclopropanes. A Straightforward Entry to Fused 6,7,5-Tricyclic Systems
    Saya, Lucia
    Fernandez, Israel
    Lopez, Fernando
    Mascarenas, Jose L.
    ORGANIC LETTERS, 2014, 16 (19) : 5008 - 5011