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Candida tenuis Xylose Reductase Catalyzed Reduction of Aryl Ketones for Enantioselective Synthesis of Active Oxetine Derivatives
Author(s) -
Vogl Michael,
Kratzer Regina,
Nidetzky Bernd,
Brecker Lothar
Publication year - 2012
Publication title -
chirality
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.43
H-Index - 77
eISSN - 1520-636X
pISSN - 0899-0042
DOI - 10.1002/chir.22082
Subject(s) - chemistry , enantioselective synthesis , xylose , aryl , catalysis , organic chemistry , stereochemistry , combinatorial chemistry , fermentation , alkyl
ABSTRACT Candida tenuis xylose reductase shows high catalytic efficiencies in carbonyl reduction of acetophenone and 1‐phenyl‐1‐propanone derivatives. The quite low substrate solubility in aqueous buffer systems is circumvented by addition of methanol or by two‐phase solvent systems. In the latter, methanol improves the substrate phase transfer as solvent mediator and leads to reasonable space/time yields. Resulting enantiomerically pure chiral alcohols are key intermediates for synthesis of active pharmaceutical ingredients. ( R )‐Atomoxetine is exemplarily synthesized in four steps, and the further use for generation of other oxetine derivatives and a polo‐like kinase 1 inhibitor are discussed. Chirality 00:000–000, 2012 . © 2012 Wiley Periodicals, Inc.