Copper(II)-catalyzed exo and enantioselective cycloadditions of azomethine imines

被引：110
|
作者：
Sibi, Mukund P. [1 ]
Rane, Digamber [1 ]
Stanley, Levi M. [1 ]
Soeta, Takahiro [1 ]
机构：
[1] N Dakota State Univ, Dept Chem, Fargo, ND 58105 USA
来源：
ORGANIC LETTERS | 2008年 / 10卷 / 14期
关键词：
D O I：
10.1021/ol800904t
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A strategy for exo and enantioselective 1,3-dipolar cycloaddition of azomethine imines to 2-acryloyl-3-pyrazolidinone is described. The corresponding cycloadducts are isolated with high diastereoselectivities (up to >96:4 exo/endo) and enantioselectivities (up to 98% ee).
引用
收藏
页码：2971 / 2974
页数：4
相关论文
共 50 条
  • [31] A new copper-catalyzed [3 + 2] cycloaddition: Enantioselective coupling of terminal alkynes with azomethine imines to generate five-membered nitrogen heterocycles
    1600, American Chemical Society (125):
  • [32] Rhodium-Catalyzed Asymmetric Arylation of Azomethine Imines
    Shintani, Ryo
    Soh, Ying-Teck
    Hayashi, Tamio
    ORGANIC LETTERS, 2010, 12 (18) : 4106 - 4109
  • [33] Chiral Phosphoric Acid-Catalyzed Enantioselective Formal [3+2] Cycloaddition of Azomethine Imines with Enecarbamates
    Wang, Yang
    Wang, Qian
    Zhu, Jieping
    CHEMISTRY-A EUROPEAN JOURNAL, 2016, 22 (24) : 8084 - 8088
  • [34] Copper(II)-catalyzed trifluoromethylation of N-aryl imines
    Zhang, Yong-Qiang
    Liu, Ji-Dan
    Xu, Hao
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2013, 11 (37) : 6242 - 6245
  • [35] Organocatalytic and stereoselective [3+2] cycloadditions of azomethine imines with α,β-unsaturated aldehydes
    Chen, Wei
    Yuan, Xiang-Hong
    Li, Rui
    Du, Wei
    Wu, Yong
    Ding, Li-Sheng
    Chen, Ying-Chun
    ADVANCED SYNTHESIS & CATALYSIS, 2006, 348 (14) : 1818 - 1822
  • [36] Copper(II)-Catalyzed Asymmetric 1,3-Dipolar [3+4] Cycloaddition and Kinetic Resolution of Azomethine Imines with Azoalkenes
    Wei, Liang
    Wang, Zuo-Fei
    Yao, Lu
    Qiu, Guofu
    Tao, Haiyan
    Li, Hua
    Wang, Chun-Jiang
    ADVANCED SYNTHESIS & CATALYSIS, 2016, 358 (24) : 3955 - 3959
  • [37] The enantioselective diethylzinc addition to imines catalyzed by chiral Cu(II)-oxazoline complexes
    Li, X
    Cun, LF
    Gong, LZ
    Mi, AQ
    Jiang, YZ
    TETRAHEDRON-ASYMMETRY, 2003, 14 (24) : 3819 - 3821
  • [38] Copper(II)-catalyzed enantioselective intramolecular carboamination of alkenes
    Zeng, Wei
    Chemler, Sherry R.
    Journal of the American Chemical Society, 2007, 129 (43): : 12948 - 12949
  • [39] Copper(II)-catalyzed enantioselective intramolecular carboamination of alkenes
    Zeng, Wei
    Chemler, Sherry R.
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (43) : 12948 - +
  • [40] "Click" Chemistry: Application of Copper Metal in Cu-Catalyzed Azomethine Imine-Alkyne Cycloadditions
    Kirar, Eva Pusavec
    Groselj, Uros
    Mirri, Giorgio
    Pozgan, Franc
    Strle, Gregor
    Stefane, Bogdan
    Jovanovski, Vasko
    Svete, Jurij
    JOURNAL OF ORGANIC CHEMISTRY, 2016, 81 (14): : 5988 - 5997
12345