Practical Two‐Step Synthesis of an Enantiopure Aliphatic Terminal ( S )‐Epoxide Based on Reduction of Haloalkanones with “Designer Cells” | Zendy

Berkessel Albrecht | Zendy; Rollmann Claudia | Zendy; Chamouleau Francoise | Zendy; Labs Stefanie | Zendy; May Oliver | Zendy; Gröger Harald | Zendy

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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 ).

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