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Practical Two‐Step Synthesis of an Enantiopure Aliphatic Terminal ( S )‐Epoxide Based on Reduction of Haloalkanones with “Designer Cells”
Author(s) -
Berkessel Albrecht,
Rollmann Claudia,
Chamouleau Francoise,
Labs Stefanie,
May Oliver,
Gröger Harald
Publication year - 2007
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.200700244
Subject(s) - enantiopure drug , chemistry , enantioselective synthesis , epoxide , epoxide hydrolase , enantiomeric excess , yield (engineering) , alcohol dehydrogenase , substrate (aquarium) , enantiomer , organic chemistry , dehydrogenase , alcohol , stereochemistry , combinatorial chemistry , enzyme , catalysis , microsome , materials science , oceanography , geology , metallurgy
A practical biocatalytic method for the synthesis of aliphatic β‐halogenated ( S )‐alcohols as epoxide precursors by means of an enantioselective reduction of the corresponding ketones with recombinant whole cells, bearing an alcohol dehydrogenase and a glucose dehydrogenase, was developed. The biotransformations operate at high substrate concentrations of up to 208 g/L, and afford the ( S )‐β‐halohydrins with both high conversions of >95 % and enantioselectivities of >99 % ee . Base‐induced cyclization of the β‐halohydrin intermediates gave the desired ( S )‐epoxides in high yield and enantiomeric purity (>99 % ee ).