Stereoinversion of 1-arylethanols by Cyanidioschyzon merolae NEIS-1332

The stereoinversion of ortho-, meta- and para-substituted fluoro, chloro, bromo and methyl 1-phenylethanols using red alga (Cyanidioschyzon merolae) was investigated. It was found that 1-(4′-chlorophenyl)ethanol (1f) gave the corresponding (S)-alcohols in high ee and high yield (95%, 91% ee). On the other hand, stereoinversion of 1-(3′-chlorophenyl)ethanol (1e) indicated moderate ee (1e, 54% ee). In the case of 1-(2′-chlorophenyl)ethanol (1d), the biotransformation did not proceed. Moreover, we discuss about stereoinversion of alkyl group for secondary alcohols (3a–3d) and cis-2-methylcyclohexanol.