Asymmetric bioreduction of a bulky ketone: 1-phenyl-1-(2-phenylthiazol-5-yl)-methanone

Citation
S. Roy et al., Asymmetric bioreduction of a bulky ketone: 1-phenyl-1-(2-phenylthiazol-5-yl)-methanone, ADV SYNTH C, 343(6-7), 2001, pp. 738-743
Citations number
29
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
ADVANCED SYNTHESIS & CATALYSIS
ISSN journal
16154150 → ACNP
Volume
343
Issue
6-7
Year of publication
2001
Pages
738 - 743
Database
ISI
SICI code
1615-4150(200108)343:6-7<738:ABOABK>2.0.ZU;2-P
Abstract
We have investigated the preparation or (R)- and (S)-1-phenyl-1-(2-phenylth iazol-5-yl)-methanol by asymmetric bioreduction of the corresponding bulky ketone 1-phenyl-1-(2-phenylthiazol-5-yl)-methanone with whole microbial cel ls. A short screening of 38 microbial strains allowed the selection of two suitable yeast strains fulfilling enantio-complementarity. Gram-scale prepa rations of the S- and R-alcohols were achieved with high yield and high opt ical purity using, respectively, Saccharomyces montanus CBS 6772 (yield 79% , ee 96%) and Rhodotorula glutinis var. dairenensis MUCL 30607 (yield 96%, ee 91 %). The two enantiomeric alcohols prepared are novel compounds descri bed here for the first time.