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Asymmetric Synthesis of N ‐Substituted α‐Amino Esters from α‐Ketoesters via Imine Reductase‐Catalyzed Reductive Amination
Author(s) -
Yao Peiyuan,
Marshall James R.,
Xu Zefei,
Lim Jesmine,
Charnock Simon J.,
Zhu Dunming,
Turner Nicholas J.
Publication year - 2021
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.202016589
Subject(s) - imine , reductive amination , chemistry , enantioselective synthesis , catalysis , enantiomer , combinatorial chemistry , amination , enantiomeric excess , biocatalysis , stereoisomerism , organic chemistry , reaction mechanism
N ‐Substituted α‐amino esters are widely used as chiral intermediates in a range of pharmaceuticals. Here we report the enantioselective biocatalyic synthesis of N ‐substituted α‐amino esters through the direct reductive coupling of α‐ketoesters and amines employing sequence diverse metagenomic imine reductases (IREDs). Both enantiomers of N ‐substituted α‐amino esters were obtained with high conversion and excellent enantioselectivity under mild reaction conditions. In addition >20 different preparative scale transformations were performed highlighting the scalability of this system.