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
  • [41] Ruthenium-Catalyzed β-Alkylation of Secondary Alcohols and α-Alkylation of Ketones via Borrowing Hydrogen: Dramatic Influence of the Pendant N-Heterocycle
    Zhang, Chong
    Zhao, Jiong-Peng
    Hu, Bowen
    Shi, Jing
    Chen, Dafa
    ORGANOMETALLICS, 2019, 38 (03) : 654 - 664
  • [42] Efficient β-alkylation of secondary alcohols to α-substituted ketones catalyzed by functionalized Ir complexes via borrowing hydrogen in water
    Liu, Xin
    Dong, Wen-Zhe
    Li, Yang
    Yu, Xiaoqiang
    Wang, Wan-Hui
    Himeda, Yuichiro
    Bao, Ming
    ORGANIC CHEMISTRY FRONTIERS, 2023, 10 (02) : 355 - 362
  • [43] Biocatalytic N-Alkylation of Amines Using Either Primary Alcohols or Carboxylic Acids via Reductive Aminase Cascades
    Ramsden, Jeremy I.
    Heath, Rachel S.
    Derrington, Sasha R.
    Montgomery, Sarah L.
    Mangas-Sanchez, Juan
    Mulholland, Keith R.
    Turner, Nicholas J.
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2019, 141 (03) : 1201 - 1206
  • [44] An Efficient Palladium-Catalyzed N-Alkylation of Amines Using Primary and Secondary Alcohols
    Tuan Thanh Dang
    Ramalingam, Balamurugan
    Shan, Siah Pei
    Seayad, Abdul Majeed
    ACS CATALYSIS, 2013, 3 (11): : 2536 - 2540
  • [45] Ruthenium-catalyzed β-alkylation of secondary alcohols with primary alcohols
    Bai, Wei
    Jia, Guochen
    INORGANICA CHIMICA ACTA, 2015, 431 : 234 - 241
  • [46] Ruthenium-Catalyzed β-Alkylation of Secondary Alcohols with Primary Alcohols
    Cheung, Hung Wai
    Lee, Ting Yan
    Lui, Ho Yin
    Yeung, Chi Hung
    Lau, Chak Po
    ADVANCED SYNTHESIS & CATALYSIS, 2008, 350 (18) : 2975 - 2983
  • [47] Ruthenium(III)-Catalyzed β-Alkylation of Secondary Alcohols with Primary Alcohols
    Wang, Qingfu
    Wu, Kaikai
    Yu, Zhengkun
    ORGANOMETALLICS, 2016, 35 (09) : 1251 - 1256
  • [48] Efficient conversion of primary and secondary alcohols to primary amines
    Sun, Weilin
    Pelletier, Jeffrey C.
    TETRAHEDRON LETTERS, 2007, 48 (44) : 7745 - 7746
  • [49] Ruthenium-catalysed N-alkylation of anilines with primary carbohydrate alcohols via borrowing hydrogen strategy
    Tsuge, Kouki
    Kubota, Shunnichi
    Sakamoto, Kana
    Kitayama, Kenji
    Nishimura, Takahiro
    CHEMICAL COMMUNICATIONS, 2023, 59 (46) : 7052 - 7055
  • [50] Iridium-CNP complex catalyzed cross-coupling of primary alcohols and secondary alcohols by a borrowing hydrogen strategy
    Wang, Dawei
    Zhao, Keyan
    Yu, Xin
    Miao, Hongyan
    Ding, Yuqiang
    RSC ADVANCES, 2014, 4 (81): : 42924 - 42929
12345