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One‐pot Chemoenzymatic Deracemisation of Secondary Alcohols Employing Variants of Galactose Oxidase and Transfer Hydrogenation
Author(s) -
Yuan Bo,
Debecker Damien P.,
Wu Xiaofeng,
Xiao Jianliang,
Fei Qiang,
Turner Nicholas J.
Publication year - 2020
Publication title -
chemcatchem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.497
H-Index - 106
eISSN - 1867-3899
pISSN - 1867-3880
DOI - 10.1002/cctc.202001191
Subject(s) - chemistry , transfer hydrogenation , galactose oxidase , alcohol , ketone , alcohol oxidation , enantiomer , enantiomeric excess , organic chemistry , ethanol , noyori asymmetric hydrogenation , aldehyde , homogeneous , combinatorial chemistry , enantioselective synthesis , enzyme , catalysis , physics , ruthenium , thermodynamics
Enantiomerically enriched chiral secondary alcohols serve as valuable building blocks for drug intermediates and fine chemicals. In this study the deracemisation of secondary alcohols to generate enantiomeric pure chiral alcohols has been achieved by combining enantio‐selective enzymatic oxidation of a secondary alcohol, by a variant of GOase (GOase M 3‐5 ), with either non‐selective ketone reduction via transfer hydrogenation (TH) or enantio‐selective asymmetric transfer hydrogenation (ATH). Both the enzymatic oxidation system and the transition‐metal mediated reduction system were optimised to ensure compatibility with each other resulting in a homogeneous reaction system. 1‐(4‐nitrophenyl)ethanol was generated with 99 % conversion and 98 % ee by the deracemisation method, and it has been extended to a series of other secondary alcohols with comparable results.