z-logo
Premium
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.

This content is not available in your region!

Continue researching here.

Having issues? You can contact us here
Accelerating Research

Address

John Eccles House
Robert Robinson Avenue,
Oxford Science Park, Oxford
OX4 4GP, United Kingdom