Direct Alkylation of Amines with Primary and Secondary Alcohols through Biocatalytic Hydrogen Borrowing

被引：85
|
作者：
Montgomery, Sarah L. [1 ]
Mangas-Sanchez, Juan [1 ]
Thompson, Matthew P. [1 ]
Aleku, Godwin A. [1 ]
Dominguez, Beatriz [2 ]
Turner, Nicholas J. [1 ]
机构：
[1] Univ Manchester, Sch Chem, Manchester Inst Biotechnol, 131 Princess St, Manchester M1 7DN, Lancs, England
[2] Johnson Matthey Catalysis & Chiral Technol, 28 Cambridge Sci Pk,Milton Rd, Cambridge CB4 0FP, England
来源：
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2017年 / 56卷 / 35期
基金：
英国生物技术与生命科学研究理事会;
关键词：
asymmetric amination; biocatalysis; enzyme cascades; reductive aminase; synthetic methods; CHIRAL PHOSPHORIC-ACID; IMINE REDUCTASES IREDS; ENANTIOSELECTIVE AMINATION; COOPERATIVE CATALYSIS; SEC-ALCOHOLS; CASCADE; METHODOLOGY; OXIDATION;
D O I：
10.1002/anie.201705848
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
The reductive aminase from Aspergillus oryzae (AspRedAm) was combined with a single alcohol dehydrogenase (either metagenomic ADH-150, an ADH from Sphingobium yanoikuyae (SyADH), or a variant of the ADH from Thermoanaerobacter ethanolicus (TeSADH W110A)) in a redox-neutral cascade for the biocatalytic alkylation of amines using primary and secondary alcohols. Aliphatic and aromatic secondary amines were obtained in up to 99 % conversion, as well as chiral amines directly from the racemic alcohol precursors in up to >97 % ee, releasing water as the only byproduct.
引用
收藏
页码：10491 / 10494
页数：4
相关论文
共 50 条
  • [31] Discovering the role of N-heterocyclic carbene as hydrogen borrowing organocatalyst: metal-free, direct N-alkylation of amines with benzyl alcohols
    Sharma, Richa
    Rahaman, T. A. Abdul
    Sen, Janmejaya
    Mashevskaya, Irina V. V.
    Chaudhary, Sandeep
    ORGANIC CHEMISTRY FRONTIERS, 2023, 10 (03): : 730 - 744
  • [32] Conversion of alcohols to enantiopure amines through dual-enzyme hydrogen-borrowing cascades
    Mutti, Francesco G.
    Knaus, Tanja
    Scrutton, Nigel S.
    Breuer, Michael
    Turner, Nicholas J.
    SCIENCE, 2015, 349 (6255) : 1525 - 1529
  • [33] Mn-catalyzed ring-opening and alkylation of epoxides with alcohols for accessing β-alkylated secondary alcohols via borrowing hydrogen
    Rong, Qiang
    Deng, Hongbin
    Sun, Nan
    Che, Anqi
    Hu, Xinquan
    Jin, Liqun
    ORGANIC CHEMISTRY FRONTIERS, 2024, 11 (24): : 7107 - 7113
  • [34] Recent Advances in α-Alkylation Reactions using Alcohols with Hydrogen Borrowing Methodologies
    Obora, Yasushi
    ACS CATALYSIS, 2014, 4 (11): : 3972 - 3981
  • [35] Cyclometalated Iridium Complex-Catalyzed N-Alkylation of Amines with Alcohols via Borrowing Hydrogen in Aqueous Media
    Luo, NianHua
    Zhong, YuHong
    Wen, HuiLing
    Luo, Renshi
    ACS OMEGA, 2020, 5 (42): : 27723 - 27732
  • [36] Ruthenium-Catalyzed N-Alkylation of Amines with Alcohols under Mild Conditions Using the Borrowing Hydrogen Methodology
    Enyong, Arrey B.
    Moasser, Bahram
    JOURNAL OF ORGANIC CHEMISTRY, 2014, 79 (16): : 7553 - 7563
  • [37] N-alkylation of amines with alcohols over alumina-entrapped Ag catalysts using the "borrowing hydrogen" methodology
    Liu, Huihui
    Chuah, Gaik-Khuan
    Jaenicke, Stephan
    JOURNAL OF CATALYSIS, 2012, 292 : 130 - 137
  • [38] Copper-Catalyzed Borrowing Hydrogen Reaction for α-Alkylation of Amides with Alcohols
    Xia, Qiuling
    Miao, Yulong
    Hu, Yue
    Xie, Yinjun
    Luo, Junfei
    JOURNAL OF ORGANIC CHEMISTRY, 2024, 89 (13): : 9654 - 9660
  • [39] Catalytic N-alkylation of primary amines with alcohols
    Shuikin, A.N.
    Glebov, L.S.
    Kliger, G.A.
    Zaikin, V.G.
    Neftekhimiya, 1993, 33 (04): : 321 - 326
  • [40] CATALYTIC N-ALKYLATION OF PRIMARY AMINES BY ALCOHOLS
    SHUIKIN, AN
    GLEBOV, LS
    KLIGER, GA
    ZAIKIN, VG
    PETROLEUM CHEMISTRY, 1993, 33 (04) : 307 - 312
12345