Regio- and Enantioselective Formal Hydroamination of Enamines for the Synthesis of 1,2-Diamines

被引:38
|
作者
Yu, Lu [1 ]
Somfai, Peter [1 ]
机构
[1] Lund Univ, Dept Chem, Ctr Anal & Synth, S-22100 Lund, Sweden
基金
瑞典研究理事会;
关键词
amines; copper; enamines; enantioselectivity; hydroamination; ANTI-MARKOVNIKOV HYDROAMINATION; CATALYTIC ASYMMETRIC DIAMINATION; METAL-FREE DIAMINATION; INTERMOLECULAR HYDROAMINATION; UNACTIVATED ALKENES; VICINAL DIAMINES; AMINES; AMINOBORATION; PALLADIUM; VINYLARENES;
D O I
10.1002/anie.201902642
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The asymmetric formal hydroamination of enamines using a CuH catalyst is reported. The method provides a straightforward and efficient approach to the synthesis of chiral 1,2-dialkyl amines in good yields with high levels of enantioselectivities for a broad range of substrates, and should have significant value for the preparation of molecules bearing a 1,2-diamine motif.
引用
收藏
页码:8551 / 8555
页数:5
相关论文
共 50 条
  • [1] Regio- and Enantioselective Synthesis of 1,2-Diamines by Formal Hydroamination of Enamines: Scope, Mechanism, and Asymmetric Synthesis of Orthogonally Protected Bis-Piperazines as a Privileged Scaffold
    Mohiti, Maziar
    Lu, Yu
    He, Hui
    Ni, Shao-Fei
    Somfai, Peter
    CHEMISTRY-A EUROPEAN JOURNAL, 2024, 30 (16)
  • [2] Regio- and Chemoselective Intermolecular Hydroamination of Allyl Imines for the Synthesis of 1,2-Diamines
    Ickes, Andrew R.
    Ensign, Seth C.
    Gupta, Anil K.
    Hull, Kami L.
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2014, 136 (32) : 11256 - 11259
  • [3] Synthesis of 1,2-Diamines via Hydroamination Reactions
    Gupta, Anil K.
    Hull, Kami L.
    SYNLETT, 2015, 26 (13) : 1779 - 1784
  • [4] Copper-Catalyzed Regio- and Enantioselective Hydroamination of Alkenes with Hydroxylamines
    Hesp, Kevin D.
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (08) : 2034 - 2036
  • [5] Regio- and Enantioselective Synthesis of 1,2-Diamine Derivatives by Copper-Catalyzed Hydroamination
    Ichikawa, Saki
    Dai, Xi-Jie
    Buchwald, Stephen L.
    ORGANIC LETTERS, 2019, 21 (11) : 4370 - 4373
  • [6] Biocatalytic formal regio- and enantioselective Markovnikov hydroamination of aryl alkenes to chiral amines
    Jin, Qi
    Zhang, Jingqi
    Huang, Shuangping
    Gao, Lili
    Chang, Honghong
    Zhang, Jiandong
    GREEN CHEMISTRY, 2023, 25 (12) : 4840 - 4848
  • [7] Regio- and Enantioselective Hydroamination of Dienes by Gold(I)/Menthol Cooperative Catalysis
    Kanno, Osamu
    Kuriyama, Wataru
    Wang, Z. Jane
    Toste, F. Dean
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (42) : 9919 - 9922
  • [8] Synthesis of α-Trifluoromethylamines by Cu-Catalyzed Regio- and Enantioselective Hydroamination of 1-Trifluoromethylaikenes
    Takata, Tatsuaki
    Hirano, Koji
    Miura, Masahiro
    ORGANIC LETTERS, 2019, 21 (11) : 4284 - 4288
  • [9] Synthesis of 1,2-Dialkylaminoethers via Photoredox Catalyzed Hydroamination of Vinylethers
    Niggli, Nadja E. E.
    Bienewald, Frank
    Kirchner, Huelya
    Shevchenko, Grigory A. A.
    Hashmi, A. Stephen K.
    Schaub, Thomas
    CHEMISTRYSELECT, 2023, 8 (26):
  • [10] Cyclohexane-1,2-diamines: Efficient Catalysts for the Enantioselective Conjugate Addition of Ketones to Nitro Olefins
    Rasappan, Ramesh
    Reiser, Oliver
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2009, 2009 (09) : 1305 - 1308