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

Abstract

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.

Update 1 of: Enantioselective Enzymatic Desymmetrizations in Organic Synthesis

“…For instance, Roy et al have investigated the preparation of (R)-and (S)-1-phenyl-1-(2-phenylthiazol-5-yl)-methanol [(R)-and (S)-224] by enantioselective bioreduction of 1-phenyl-1-(2-phenylthiazol-5-yl)-methanone with whole microbial cells (Scheme 44). 190 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 in good to high optical purity and high yield using, respectively, Saccharomyces montanus CBS 6772 and Rhodotorula glutinis var.…”

Novel Developments Employing Redox Enzymes: Old Enzymes in New Clothes

“…For efficient screening, readily prepared libraries of microbial strains are used to identify suitable microorganisms quickly [31][32][33][34][35][36][37]. Besides fungi, yeasts, and bacterial strains, algae and plant cells proved to be applicable (Table 1, entries 2 and 5, respectively) [38].…”

Enantioselective Bioreduction of Prochiral Pyrimidine Base Derivatives by Boni Protect Fungicide Containing Live Cells of Aureobasidium pullulans

“…Baker's yeast is the most popular whole-cell biocatalyst for the asymmetric reduction of prochiral ketones due to its unlimited availability, ease of growing, and low cost [7]. For asymmetric bioreduction of ketones, in addition to the popular Baker's yeast, most often the cells of bacterial [8], fungal [9][10][11][12][13], and plant tissue [14][15][16][17] are used. The application of bioreagents in enantioselective enzymatic desymmetrization of prochiral ketones leads to a broad spectrum of chiral alcohols used as intermediates in the syntheses of many pharmaceuticals and compounds presenting biological activity [6].…”