Lipase AK-Mediated Synthesis of Both Antipodes of 2-Phenyl- and 2-(1-Naphthyl)cyclohexanols in Enantiomerically Pure Form

Abstract

Both (R,S)- and (S,R)-enantiomers of 2-phenylcyclohexanol and 2-(1-naphthyl)cyclohexanol were prepared in enantiomerically pure form and in excellent chemical yields by lipase AK (Pseudomonas fluorescens)-catalyzed kinetic acetylation of racemic alcohols with vinyl acetate in t-butyl methyl ether at 35 °C. The enantioselectivity of this biocatalytic transformation was found to be independent of reaction time.

Key words

lipase AK - kinetic acetylation - pure enantiomers - 2-phenylcyclohexanol - 2-(1-naphthyl)cyclohexanol

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