Ruthenium-catalyzed ring-opening and ring-closing enyne metathesis

被引:82
|
作者
Kitamura, T [1 ]
Mori, R [1 ]
机构
[1] Hokkaido Univ, Grad Sch Pharmaceut Sci, Sapporo, Hokkaido 0600812, Japan
关键词
D O I
10.1021/ol015606m
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
When a CH2Cl2 solution of an enyne containing the cycloalkene moiety was stirred in the presence of ruthenium-carbene complex (10 mol %) at room temperature under ethylene gas (1 atm), ring-opening and ring closing metathesis occurred to afford cyclized triene. The reaction was carried out under argon gas, and no cyclized product was obtained. Enynes with a terminal alkyne gave good results.
引用
收藏
页码:1161 / 1163
页数:3
相关论文
共 50 条
  • [21] Supported Catalysts Useful in Ring-Closing Metathesis, Cross Metathesis, and Ring-Opening Metathesis Polymerization
    Suriboot, Jakkrit
    Bazzi, Hassan S.
    Bergbreiter, David E.
    [J]. POLYMERS, 2016, 8 (04)
  • [22] Enyne ring-closing metathesis on heteroaromatic cations
    Nunez, Ana
    Cuadro, Ana M.
    Alvarez-Builla, Julio
    Vaquero, Juan J.
    [J]. CHEMICAL COMMUNICATIONS, 2006, (25) : 2690 - 2692
  • [23] Ruthenium-catalyzed ring-closing metathesis on alkene-tethered Fischer carbene complexes
    Hazra, D
    Sarkar, A
    [J]. INDIAN JOURNAL OF CHEMISTRY SECTION A-INORGANIC BIO-INORGANIC PHYSICAL THEORETICAL & ANALYTICAL CHEMISTRY, 2003, 42 (09): : 2398 - 2405
  • [24] Synthesis and Cytotoxicity Evaluation of Betulin Cycloolefin Derivatives by Ruthenium-Catalyzed Ring-Closing Metathesis
    Lin, Jiahui
    Zhu, Zihao
    Chen, Yuwen
    Zuo, Weiwei
    Zhu, Meifang
    Ma, Zhiyuan
    [J]. JOURNAL OF NATURAL PRODUCTS, 2023, 86 (04): : 842 - 849
  • [25] An Approach to the Synthesis of Pyrimido[b]azepines via Ruthenium-Catalyzed Ring-Closing Metathesis
    Zhang, Tong-Bo
    Yang, Quan-Zhi
    Cao, Yuan-Yuan
    Wu, Shao-Tong
    Zhang, Yu
    Guo, Ying
    Zhao, Jian-Xiong
    Sun, Xue-Feng
    Zhang, Zhi-Li
    Tian, Chao
    Liu, Jun-Yi
    Wang, Xiao-Wei
    [J]. SYNTHESIS-STUTTGART, 2015, 47 (21): : 3292 - 3300
  • [26] Ruthenium-catalyzed ring-closing metathesis accelerated by long-range steric effect
    Fujihara, Tetsuaki
    Tomike, Yoshikazu
    Ohtake, Toshiyuki
    Terao, Jun
    Tsuji, Yasushi
    [J]. CHEMICAL COMMUNICATIONS, 2011, 47 (34) : 9699 - 9701
  • [27] Synthesis of 3-Hydroxypyridines Using Ruthenium-Catalyzed Ring-Closing Olefin Metathesis
    Yoshida, Kazuhiro
    Kawagoe, Fumihiro
    Hayashi, Kazushi
    Horiuchi, Shingo
    Imamoto, Tsuneo
    Yanagisawa, Akira
    [J]. ORGANIC LETTERS, 2009, 11 (03) : 515 - 518
  • [28] Total Synthesis of (+)-Clavilactone A and (-)-Clavilactone B by Ring-Opening/Ring-Closing Metathesis
    Takao, Ken-ichi
    Nanamiya, Ryuki
    Fukushima, Yuuki
    Namba, Ayumi
    Yoshida, Keisuke
    Tadano, Kin-ichi
    [J]. ORGANIC LETTERS, 2013, 15 (21) : 5582 - 5585
  • [29] Alkyne metathesis as a new synthetic tool: Ring-closing, ring-opening, and acyclic
    Bunz, UHF
    Kloppenburg, L
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1999, 38 (04) : 478 - 481
  • [30] Ruthenium-Catalyzed Tandem Ring-Opening/Ring-Closing/Cross-Metathesis of 1,6-Cyclopropene-ynes and Olefins for the Construction of the 3-Pyrroline Skeleton
    Zhu, Zhi-Bin
    Shi, Min
    [J]. ORGANIC LETTERS, 2010, 12 (20) : 4462 - 4465