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Stereoselective Oxidation of 1‐Phenyl‐1,2‐propanediol Mediated by Microorganisms
Author(s) -
Martins Rodrigo S.,
Zampieri Dávila S.,
Rodrigues J. Augusto R.,
Carvalho Patrícia O.,
Moran Paulo J. S.
Publication year - 2011
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.201100145
Subject(s) - geotrichum , micrococcus luteus , kinetic resolution , yield (engineering) , enantioselective synthesis , biocatalysis , chemistry , yeast , enantiomeric excess , microorganism , candida albicans , stereochemistry , stereoselectivity , organic chemistry , catalysis , bacteria , biology , botany , biochemistry , reaction mechanism , escherichia coli , food science , materials science , genetics , metallurgy , gene
Abstract The enantioselective oxidation of (1 R ,2 S )‐1‐phenyl‐1,2‐propanediol [(1 R ,2 S )‐ 1 ], mediated by baker’s yeast, gave (−)‐( S )‐1‐phenyl‐2‐hydroxy‐1‐propanone [( S )‐ 2 ] in 64 % isolated yield and 93 % ee . Kinetic experiments of the bio‐oxidation of (±)‐ anti ‐ 1 revealed that the enantiomer (1 R ,2 S )‐ 1 was more reactive than (1 S ,2 R )‐ 1. Therefore, this result allowed us to devise a kinetic resolution experiment to obtain (1 S ,2 R )‐ 1 in >99 % ee from (±)‐ anti ‐ 1 . The preparation of (1 S ,2 R )‐ 1 is interesting, as it is the antipode of the product obtained by the reduction of 1‐phenyl‐1,2‐propanedione using baker’s yeast. Other microorganisms, such as Micrococcus luteus, Candida albicans, and Geotrichum candidum, were also used for kinetic resolution experiments of (±)‐ anti ‐ 1 . The best result was obtained using Geotrichum candidum , which gave (1 S ,2 R )‐ 1 in 32 % yield and 99 % ee .