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
收藏
页码:2431 / 2434
页数:4
相关论文
共 50 条
  • [21] Regio- and stereoselective synthesis of cyclobutanes by nickel-catalyzed homodimerizative [2+2] cycloaddition using allenamides
    Kawata, Yuna
    Arai, Shigeru
    Nakajima, Masaya
    Nishida, Atsushi
    TETRAHEDRON LETTERS, 2021, 69
  • [22] Enantioselective Ficini Reaction: Ruthenium/PNNP-Catalyzed [2+2] Cycloaddition of Ynamides with Cyclic Enones
    Schotes, Christoph
    Mezzetti, Antonio
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (13) : 3072 - 3074
  • [23] DFT Study on Rhodium-Catalyzed Intermolecular [2+2] Cycloaddition of Terminal Alkynes with Electron-Deficient Alkenes
    Zhao, Liu
    Zhang, Lei
    Fang, De-Cai
    ORGANOMETALLICS, 2016, 35 (20) : 3577 - 3586
  • [24] Alkynyl halides in ruthenium(II)-catalyzed [2+2] cycloadditions of bicyclic alkenes
    Allen, Anna
    Villeneuve, Karine
    Cockburn, Neil
    Fatila, Elisabeth
    Riddell, Nicole
    Tam, William
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2008, 2008 (24) : 4178 - 4192
  • [25] Nickel-catalyzed [2+2+2] Cycloaddition Reaction of Isocyanates with 1,3-Dienes
    Morimoto, Masao
    Nishida, Yui
    Miura, Tomoya
    Murakami, Masahiro
    CHEMISTRY LETTERS, 2013, 42 (05) : 550 - 552
  • [26] Nickel-Catalyzed [2+2+2] Cycloaddition of Alkyne-Nitriles with Alkynes Assisted by Lewis Acids: Efficient Synthesis of Fused Pyridines
    You, Xu
    Xie, Xin
    Wang, Gaonan
    Xiong, Meijun
    Sun, Renhong
    Chen, Haoyi
    Liu, Yuanhong
    CHEMISTRY-A EUROPEAN JOURNAL, 2016, 22 (47) : 16764 - 16768
  • [27] Nickel-Catalyzed [3+2+2] Cycloadditions between Alkynylidenecyclopropanes and Activated Alkenes
    Saya, Lucia
    Bhargava, Gaurav
    Navarro, Miguel A.
    Gulias, Moises
    Lopez, Fernando
    Fernandez, Israel
    Castedo, Luis
    Mascarenas, Jose L.
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2010, 49 (51) : 9886 - 9890
  • [28] Nickel-Catalyzed Enantioselective Synthesis of Cyclobutenes via [2+2] Cycloaddition of α,β-Unsaturated Carbonyls with 1,3-Enynes
    Kumar, Ravindra
    Tamai, Eri
    Ohnishi, Akira
    Nishimura, Akira
    Hoshimoto, Yoichi
    Ohashi, Masato
    Ogoshi, Sensuke
    SYNTHESIS-STUTTGART, 2016, 48 (17): : 2789 - 2794
  • [29] Chiral Guanidine/Copper Catalyzed Asymmetric Azide-Alkyne Cycloaddition/[2+2] Cascade Reaction
    Guo, Songsong
    Dong, Pei
    Chen, Yushuang
    Feng, Xiaoming
    Li, Xiaohua
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2018, 57 (51) : 16852 - 16856
  • [30] Synthesis of Cyclobutanones by Gold(I)-Catalyzed [2+2] Cycloaddition of Ynol Ethers with Alkenes
    Zanini, Margherita
    Cataffo, Andrea
    Echavarren, Antonio M.
    ORGANIC LETTERS, 2021, 23 (22) : 8989 - 8993