Stereoselective production of (S)-1-aralkyl- and 1-arylethanols by freshly harvested and lyophilized yeast cells

Substituted (S)-1-phenyl- 2a–h and (S)-1-benzyl-propan-2-ols 4a and b, and (S)-1-phenylethanol 6 were produced from prochiral ketones 1a–h, 3a,b and 5 by reductions with freshly harvested Zygosaccharomyces rouxii and Debaryomyces hansenii cells. The bioreductions were also performed by lyophilized cells. Comparison of the secondary alcohols from the bioreductions 2b–e,g,h and 4a and authentic (S)-alcohols (S)-2b–e,g,h and (S)-4a synthesized from enantiopure (S)-methyloxirane 7 proved the absolute configuration of the products.

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(S)-1-Phenylpropan-2-olC9H12OEe >99% (by HPLC on chiral column)[α]D25=+42.2 (c 1.0, CHCl3)Source of chirality: yeast-mediated reductionAbsolute configuration: S

(S)-1-(2-Methoxyphenyl)propan-2-olC10H14O2Ee >93% (by HPLC on chiral column)[α]D25=+39.8 (c 1.0, CHCl3)Source of chirality: yeast-mediated reductionAbsolute configuration: S

(S)-1-(3-Methoxyphenyl)propan-2-olC10H14O2Ee >93% (by HPLC on chiral column)[α]D25=+30.3 (c 1.0, CHCl3)Source of chirality: yeast-mediated reductionAbsolute configuration: S

(S)-1-(4-Methoxyphenyl)propan-2-olC10H14O2Ee >99% (by HPLC on chiral column)[α]D25=+34.9 (c 1.0, CHCl3)Source of chirality: yeast-mediated reductionAbsolute configuration: S

(S)-1-(2,4-Dimethoxyphenyl)propan-2-olC11H16O3Ee >99% (by HPLC on chiral column)[α]D25=+19.7 (c 1.0, CHCl3)Source of chirality: yeast-mediated reductionAbsolute configuration: S

(S)-1-(4-Chlorophenyl)propan-2-olC9H11ClOEe >99%(by HPLC on chiral column)[α]D25=+31.0 (c 1.0, CHCl3)Source of chirality: yeast-mediated reductionAbsolute configuration: S

(S)-1-Phenylbutan-2-olC10H14OEe >93% (by HPLC on chiral column)[α]D25=+12.3 (c 1.0, CHCl3)Source of chirality: yeast-mediated reductionAbsolute configuration: S