Asymmetric Reductive Amination in Organocatalysis and Biocatalysis

被引:8
|
作者
Li, Tingting [1 ]
Zhou, Qian [1 ]
Meng, Fanjing [1 ]
Cui, Wenhui [1 ]
Li, Qian [1 ]
Zhu, Jiang [2 ]
Cao, Yang [1 ]
机构
[1] Jiangsu Ocean Univ, Jiangsu Key Lab Marine Pharmaceut Cpd Screening, Lianyungang 222005, Jiangsu, Peoples R China
[2] Chinese Acad Sci, Innovat Acad Precis Measurement Sci & Technol, Natl Ctr Magnet Resonance Wuhan, State Key Lab Magnet Resonance & Atom & Mol Phys, Wuhan 430071, Peoples R China
关键词
asymmetric reductive amination; biocatalysis; chiral amines; metal-free; organocatalysis; CATALYZED TRANSFER HYDROGENATION; ENANTIOSELECTIVE SYNTHESIS; AMINE DEHYDROGENASE; OCTOPINE DEHYDROGENASE; REACTION-MECHANISM; HANTZSCH ESTER; IMINES; KETONES; TETRAHYDROQUINOLINES; PURIFICATION;
D O I
10.1002/ejoc.202300507
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
This review summarizes the recent progress of organocatalytic and biocatalytic asymmetric reductive amination (ARA), a challenging but important topic for drug discovery and the pharmaceutical industry. At present, ARA can be divided into three categories: metal catalysis, organic catalysis, and biocatalysis. In the past decade, transition metal-catalysed ARA has been well established. Organocatalytic ARA has emerged as a powerful alternative to metal-catalysed ARA, the hydrogen sources used in organocatalytic ARA are usually Hantzsch esters, benzothiazolines, boranes, and hydrosilanes, which require Lewis base or phosphoric acid catalysts to activate them to give secondary chiral amines. It is worth mentioning that biocatalytic ARA has made remarkable progress in the last decade, amino acid dehydrogenases, amine dehydrogenases, opine dehydrogenases and imine reductases have been successfully used in ARA.
引用
收藏
页数:19
相关论文
共 50 条
  • [21] A family of native amine dehydrogenases for the asymmetric reductive amination of ketones
    Ombeline Mayol
    Karine Bastard
    Lilian Beloti
    Amina Frese
    Johan P. Turkenburg
    Jean-Louis Petit
    Aline Mariage
    Adrien Debard
    Virginie Pellouin
    Alain Perret
    Véronique de Berardinis
    Anne Zaparucha
    Gideon Grogan
    Carine Vergne-Vaxelaire
    Nature Catalysis, 2019, 2 : 324 - 333
  • [22] Direct Catalytic Asymmetric Reductive Amination of Simple Aromatic Ketones
    Chang, Mingxin
    Liu, Shaodong
    Huang, Kexuan
    Zhang, Xumu
    ORGANIC LETTERS, 2013, 15 (17) : 4354 - 4357
  • [23] Asymmetric organocatalysis
    Houk, KN
    List, B
    ACCOUNTS OF CHEMICAL RESEARCH, 2004, 37 (08) : 487 - 487
  • [24] Asymmetric Organocatalysis
    Li Nan
    Liu Weijun
    Gong Liuzhu
    PROGRESS IN CHEMISTRY, 2010, 22 (07) : 1362 - 1379
  • [25] Asymmetric organocatalysis
    Seayad, J
    List, B
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2005, 3 (05) : 719 - 724
  • [26] Asymmetric organocatalysis
    Jaroch, Stefan
    Weinmann, Hilmar
    Zeitler, Kirsten
    CHEMMEDCHEM, 2007, 2 (09) : 1261 - 1264
  • [27] Asymmetric organocatalysis
    Pellissier, Helene
    TETRAHEDRON, 2007, 63 (38) : 9267 - 9331
  • [28] Asymmetric Organocatalysis
    Liu, W. J.
    Li, N.
    Gong, L. Z.
    ASYMMETRIC CATALYSIS FROM A CHINESE PERSPECTIVE, 2011, 36 : 153 - 205
  • [29] Asymmetric Stepwise Reductive Amination of Sulfonamides, Sulfamates, and a Phosphinamide by Nickel Catalysis
    Zhao, Xiaohu
    Xu, Haiyan
    Huang, Xiaolei
    Zhou, Jianrong Steve
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2019, 58 (01) : 292 - 296
  • [30] Enantioselective synthesis of tetrahydroisoquinolines via catalytic intramolecular asymmetric reductive amination
    Liu, Ruixia
    Han, Jingkuo
    Li, Bin
    Liu, Xian
    Wei, Zhao
    Wang, Jiaxin
    Wang, Qiaofeng
    Jiang, Ru
    Nie, Huifang
    Zhang, Shengyong
    ORGANIC CHEMISTRY FRONTIERS, 2021, 8 (09) : 1930 - 1934