Asymmetric Bioreduction of a Bulky Ketone: 1-Phenyl-1-(2-phenylthiazol-5-yl)-methanone

• Published in: Advanced synthesis & catalysis Vol. 343; no. 6-7; pp. 738 - 743
• Main Authors: Roy, Sébastien, Alexandre, Vanessa, Neuwels, Michel, Le Texier, Laurence
• Format: Journal Article
• Language: English
• Published: Weinheim WILEY-VCH Verlag 01.08.2001; WILEY‐VCH Verlag
• Subjects: Asymmetry; biocatalysis; bioreduction; Catalysis; enantioselectivity; fermentation; Ketones; Microorganisms; Saccharomyces; Screening; Strain; Synthesis; yeast strains
• ISSN: 1615-4150; 1615-4169
• DOI: 10.1002/1615-4169(200108)343:6/7<738::AID-ADSC738>3.0.CO;2-2

We have investigated the preparation of (R)‐ and (S)‐1‐phenyl‐1‐(2‐phenylthiazol‐5‐yl)‐methanol by asymmetric bioreduction of the corresponding bulky ketone 1‐phenyl‐1‐(2‐phenylthiazol‐5‐yl)‐methanone with whole microbial cells. A short screening of 38 microbial strains allowed the selection of two suitable yeast strains fulfilling enantiocomplementarity. Gram‐scale preparations of the S‐ and R‐alcohols were achieved with high yield and high optical 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 described here for the first time.