Enzymatic resolution of homoallyllic alcohols using various Rhizopus species

The asymmetric resolution of various 1-aryl-3-buten-1-ols via microbial hydrolysis of the corresponding acetates has been investigated using different Rhizopus species. The chosen species, R. arrhizus (wild type), efficiently hydrolyzed 1-phenyl- and 1-para-substituted phenyl-3-buten-1-ol acetates, producing the enantiomerically pure (R)-alcohols with 53-65% yields. Although the antipode acetates were obtained with 9-52% enantiomeric excess, the (S)-alcohols were amenable in >99% enantiomeric excess via a R. arrhizus mediated asymmetric reduction of the corresponding ketones.