Highly asymmetric cobalt-catalyzed aziridination of alkenes with trichloroethoxysulfonyl azide (TcesN3)

被引:114
|
作者
Subbarayan, Velusamy [1 ]
Ruppel, Joshua V. [1 ]
Zhu, Shifa [1 ]
Perman, Jason A. [1 ]
Zhang, X. Peter [1 ]
机构
[1] Univ S Florida, Dept Chem, Tampa, FL 33620 USA
关键词
C-H AMINATION; SILYL ENOL ETHERS; ENANTIOSELECTIVE AZIRIDINATION; OLEFIN AZIRIDINATION; ARYL AZIDES; DIPHENYLPHOSPHORYL AZIDE; ARYLSULFONYL AZIDES; NITRENE PRECURSORS; COPPER-COMPLEXES; NITROGEN-SOURCES;
D O I
10.1039/b905727g
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A Co(II)-based catalytic system has been developed for asymmetric aziridination of alkenes with trichloroethoxysulfonyl azide (TcesN(3)) under mild conditions, forming the corresponding N-Tces-aziridines in high yields and excellent enantioselectivities.
引用
收藏
页码:4266 / 4268
页数:3
相关论文
共 50 条
  • [1] Cobalt-catalyzed asymmetric olefin aziridination with diphenylphosphoryl azide
    Jones, Jess E.
    Ruppel, Joshua V.
    Gao, Guang-Yao
    Moore, Thomas M.
    Zhang, X. Peter
    JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (18): : 7260 - 7265
  • [2] Cobalt-catalyzed efficient aziridination of alkenes
    Gao, GY
    Harden, JD
    Zhang, XP
    ORGANIC LETTERS, 2005, 7 (15) : 3191 - 3193
  • [3] Asymmetric cobalt-catalyzed aziridination with azides as nitrene source
    Ruppel, Joshua V.
    Subbarayan, Velusamy
    Jones, Jess E.
    Zhang, X. Peter
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2009, 238
  • [4] Highly Enantioselective Cobalt-Catalyzed Hydrosilylation of Alkenes
    Cheng, Biao
    Lu, Peng
    Zhang, Heyi
    Cheng, Xinpeng
    Lu, Zhan
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2017, 139 (28) : 9439 - 9442
  • [5] Cobalt-catalyzed aziridination with diphenylphosphoryl azide (DPPA):: Direct synthesis of N-phosphorus-substituted aziridines from alkenes
    Gao, Guang-Yao
    Jones, Jess E.
    Vyas, Renu
    Harden, Jeremiah D.
    Zhang, X. Peter
    JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (17): : 6655 - 6658
  • [6] Iron- and Cobalt-Catalyzed Asymmetric Hydrofunctionalization of Alkenes and Alkynes
    Guo, Jun
    Cheng, Zhaoyang
    Chen, Jianhui
    Chen, Xu
    Lu, Zhan
    ACCOUNTS OF CHEMICAL RESEARCH, 2021, 54 (11) : 2701 - 2716
  • [7] Cobalt-catalyzed HAT reaction for asymmetric hydrofunctionalization of alkenes and nucleophiles
    Zhang, Ge
    Zhang, Qian
    CHEM CATALYSIS, 2023, 3 (03):
  • [8] Azole-Directed Cobalt-Catalyzed Asymmetric Hydrogenation of Alkenes
    Jin, Yue
    Zou, Yashi
    Hu, Yanhua
    Han, Yunxi
    Zhang, Zhenfeng
    Zhang, Wanbin
    CHEMISTRY-A EUROPEAN JOURNAL, 2022, 28 (44)
  • [9] Cobalt-catalyzed hydroarylation of alkenes
    Sanders, Tyler M.
    Perry, Marc C.
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2014, 247
  • [10] Cobalt-catalyzed dimerization of alkenes
    Wang, CC
    Lin, PS
    Cheng, CH
    TETRAHEDRON LETTERS, 2004, 45 (32) : 6203 - 6206