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

被引:36
|
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] 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
  • [5] Ring Opening of a Trisubstituted Aziridine With Amines: Regio- and Stereoselective Formation of Substituted 1,2-Diamines
    Kelley, Brandon T.
    Joullie, Madeleine M.
    ORGANIC LETTERS, 2010, 12 (19) : 4244 - 4247
  • [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] SYNTHESIS OF CHIRAL 1,2-DIAMINES
    BRUNI, E
    CARDILLO, G
    ORENA, M
    SANDRI, S
    TOMASINI, C
    TETRAHEDRON LETTERS, 1989, 30 (13) : 1679 - 1682
  • [8] Preparation of Chiral Photosensitive Organocatalysts and Their Application for the Enantioselective Synthesis of 1,2-Diamines
    Lyu, Jiyuan
    Claraz, Aurelie
    Vitale, Maxime R.
    Allain, Clemence
    Masson, Geraldine
    JOURNAL OF ORGANIC CHEMISTRY, 2020, 85 (20): : 12843 - 12855
  • [9] Computational redesign of enzymes for regio- and enantioselective hydroamination
    Ruifeng Li
    Hein J. Wijma
    Lu Song
    Yinglu Cui
    Marleen Otzen
    Yu’e Tian
    Jiawei Du
    Tao Li
    Dingding Niu
    Yanchun Chen
    Jing Feng
    Jian Han
    Hao Chen
    Yong Tao
    Dick B. Janssen
    Bian Wu
    Nature Chemical Biology, 2018, 14 : 664 - 670
  • [10] Computational redesign of enzymes for regio- and enantioselective hydroamination
    Li, Ruifeng
    Wijma, Hein J.
    Song, Lu
    Cui, Yinglu
    Otzen, Marleen
    Tian, Yu'e
    Du, Jiawei
    Li, Tao
    Niu, Dingding
    Chen, Yanchun
    Feng, Jing
    Han, Jian
    Chen, Hao
    Tao, Yong
    Janssen, Dick B.
    Wu, Bian
    NATURE CHEMICAL BIOLOGY, 2018, 14 (07) : 664 - +