Zn(II)-catalyzed asymmetric [3+2] cycloaddition of acyclic enones with azomethine ylides

被引:1
|
作者
Kumar, Sundaravel Vivek [1 ]
Olusegun, Jeremiah [1 ]
Guiry, Patrick J. [1 ]
机构
[1] Univ Coll Dublin, Ctr Synth & Chem Biol, Sch Chem, Belfield, Dublin, Ireland
基金
爱尔兰科学基金会;
关键词
1,3-DIPOLAR CYCLOADDITION; PYRROLIDINES; INDOLIZIDINE; ALKALOIDS; PROLINE;
D O I
10.1039/d4ob00854e
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The Zn(II)/UCD-Imphanol-catalyzed highly endo-selective [3 + 2] asymmetric cycloaddition of acyclic enones and azomethine ylides has been developed. Moderate to high yields (up to 94%) with excellent endo/exo selectivities (99 : 1) and enantioselectivities up to 96.5 : 3.5 er were obtained.
引用
收藏
页数:7
相关论文
共 50 条
  • [1] CuI-Catalyzed Asymmetric [3+2] Cycloaddition of Azomethine Ylides with Cyclobutenones
    Corpas, Javier
    Ponce, Alberto
    Adrio, Javier
    Carretero, Juan C.
    ORGANIC LETTERS, 2018, 20 (11) : 3179 - 3182
  • [2] Bifunctional AgOAc-catalyzed asymmetric [3+2] cycloaddition of azomethine ylides
    Zeng, W
    Zhou, YG
    ORGANIC LETTERS, 2005, 7 (22) : 5055 - 5058
  • [3] Copper(I)-catalyzed asymmetric exo-selective [3+2] cycloaddition of azomethine ylides with β-trifluoromethyl β, β-disubstituted enones
    Xu, Bing
    Zhang, Zhan-Ming
    Liu, Bing
    Xu, Shan
    Zhou, Lu-Jia
    Zhang, Junliang
    CHEMICAL COMMUNICATIONS, 2017, 53 (58) : 8152 - 8155
  • [4] Ming-Phos/Copper(I)-Catalyzed Asymmetric Intermolecular [3+2] Cycloaddition of Azomethine Ylides with Trifluoromethyl Enones
    Wu, Lizuo
    Zhang, Fengyuan
    Zhang, Zhentao
    Shang, Lei
    Liu, Yu
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2020, 40 (08) : 2460 - 2467
  • [5] Thiourea-catalyzed asymmetric formal [3+2] cycloaddition of azomethine ylides with nitroolefins
    Xie, Jianwu
    Yoshida, Kohzo
    Takasu, Kiyosei
    Takemoto, Yoshiji
    TETRAHEDRON LETTERS, 2008, 49 (48) : 6910 - 6913
  • [6] Highly Selective Copper-Catalyzed Asymmetric [3+2] Cycloaddition of Azomethine Ylides with Acyclic 1,3-Dienes
    Gonzalez-Esguevillas, Maria
    Pascual-Escudero, Ana
    Adrio, Javier
    Carretero, Juan C.
    CHEMISTRY-A EUROPEAN JOURNAL, 2015, 21 (12) : 4561 - 4565
  • [7] Ming-Phos/Copper(I)-Catalyzed Asymmetric [3+2] Cycloaddition of Azomethine Ylides with Nitroalkenes
    Zhang, Ronghua
    Xu, Bing
    Zhang, Zhanming
    Zhang, Junliang
    ACTA CHIMICA SINICA, 2020, 78 (03) : 245 - 249
  • [8] Diastereo- and Enantioselective Copper(I)-Catalyzed Intermolecular [3+2] Cycloaddition of Azomethine Ylides with β-Trifluoromethyl β,β-Disubstituted Enones
    Zhang, Zhan-Ming
    Xu, Bing
    Xu, Shan
    Wu, Hai-Hong
    Zhang, Junliang
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2016, 55 (21) : 6324 - 6328
  • [9] Asymmetric BrOnsted Base Catalyzed and Directed [3+2] Cycloaddition of 2-Acyl Cycloheptatrienes with Azomethine Ylides
    Lauridsen, Vibeke H.
    Ibsen, Lise
    Blom, Jakob
    Jorgensen, Karl Anker
    CHEMISTRY-A EUROPEAN JOURNAL, 2016, 22 (10) : 3259 - 3263
  • [10] Highly enantioselective Ag(I)-catalyzed [3+2] cycloaddition of azomethine ylides
    Longmire, JM
    Wang, B
    Zhang, XM
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (45) : 13400 - 13401