Nickel-Catalyzed Asymmetric [2+2] Cycloaddition Reaction of Hetero-Bicyclic Alkenes with Internal Alkynes

被引:27
|
作者
Qin, Hongyu [1 ]
Chen, Jingchao [1 ]
Li, Kangkui [1 ]
He, Zhenxiu [1 ]
Zhou, Yongyun [1 ]
Fan, Baomin [1 ,2 ]
机构
[1] Yunnan Minzu Univ, YMU HKBU Joint Lab Tradit Nat Med, Yuehua St, Kunming 650500, Yunnan, Peoples R China
[2] Key Lab Chem Ethn Med Resources, Yuehua St, Kunming 650500, Yunnan, Peoples R China
基金
中国国家自然科学基金;
关键词
alkynes; asymmetric catalysis; azabenzonorbornadiene; cycloaddition; oxabenzonorbornadiene; RING-OPENING REACTIONS; OXABICYCLIC ALKENES; RUTHENIUM(II)-CATALYZED CYCLIZATION; CYCLOBUTANE DERIVATIVES; PHOSPHORUS LIGANDS; ORGANIC-SYNTHESIS; HYDROGENATION; ACID; AZABENZONORBORNADIENES; ALCOHOLS;
D O I
10.1002/asia.201800492
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Enantioselective [2+2] cycloaddition reaction of azabenzonorbornadienes and oxabenzonorbornadienes with internal alkynes has been enabled by a catalyst system comprising Ni(COD)(2) and (R)-SIPHOS-Ph-Mor. This transformation represents the first asymmetric [2+2] cycloaddition reaction of azabenzonorbornadienes with internal alkynes, providing a straightforward method to prepare four-membered carbocycles.
引用
下载
收藏
页码:2431 / 2434
页数:4
相关论文
共 50 条
  • [1] Nickel-Catalyzed Reductive [2+2] Cycloaddition of Alkynes
    Canellas, Santiago
    Montgomery, John
    Pericas, Miguel A.
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2018, 140 (50) : 17349 - 17355
  • [2] Nickel-Catalyzed Intermolecular [2+2] Cycloaddition of Conjugated Enynes with Alkenes
    Nishimura, Akira
    Ohashi, Masato
    Ogoshi, Sensuke
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (38) : 15692 - 15695
  • [3] Nickel-catalyzed [2+2] cycloaddition reaction using bisallenes
    Arai, Shigeru
    Kawata, Yuna
    Amako, Yuka
    Nishida, Atsushi
    TETRAHEDRON LETTERS, 2019, 60 (43)
  • [4] 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
  • [5] Transition Metal-Catalyzed [2+2] Cycloaddition Reactions between Bicyclic Alkenes and Alkynes
    Tam, William
    Goodreid, Jordan
    Cockburn, Neil
    CURRENT ORGANIC SYNTHESIS, 2009, 6 (03) : 219 - 238
  • [6] Progress in ruthenium-catalyzed [2+2] cycloaddition reactions between bicyclic alkenes and alkynes
    Hu, Ping
    Long, Yu-hua
    Wang, Hui
    Mo, Hai-Hong
    Yang, Ding-Qiao
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2008, 28 (07) : 1181 - 1192
  • [7] Nickel-catalyzed [2+2] cycloaddition of alkynes with activated cyclic alkenes: Synthesis and novel ring expansion studies of cyclobutene products
    Huang, DJ
    Rayabarapu, DK
    Li, LP
    Sambaiah, T
    Cheng, CH
    CHEMISTRY-A EUROPEAN JOURNAL, 2000, 6 (20) : 3706 - 3713
  • [8] Intermolecular [2+2] Cycloaddition of Alkynes with Alkenes Catalyzed by Gold(I)
    Elena de Orbe, M.
    Echavarren, Antonio M.
    ORGANIC SYNTHESES, 2016, 93 : 115 - +
  • [9] Gold(I)-Catalyzed Intermolecular [2+2] Cycloaddition of Alkynes with Alkenes
    Lopez-Carrillo, Veronica
    Echavarren, Antonio M.
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (27) : 9292 - 9294
  • [10] Nickel-catalyzed [2+2] Cycloaddition Reaction of Bulky Enones with Simple Alkynes. The Effect of Bulkiness of Substituent Attached at β-Carbon
    Abulimiti, Abudoukadeer
    Nishimura, Akira
    Ohashi, Masato
    Ogoshi, Sensuke
    CHEMISTRY LETTERS, 2013, 42 (08) : 904 - 905