Enantioconvergent transformation of racemic cis-β-alkyl substituted styrene oxides to (R,R) threo diols by microsomal epoxide hydrolase catalysed hydrolysis

Article abstract of DOI:10.1016/0957-4166(95)00436-X

Both enantiomers of cis-β-ethyl, β-n-propyl, β-n-butyl, and β-n-hexyl substituted styrene oxides undergo microsomal epoxide hydrolase catalysed hydration at the (S) carbon to give the corresponding (R, R) threo diols in a > 90% e.e. A complete kinetic resolution of the racemic epoxide is also obtained with the β-ethyl substituted substrate, but not with its higher homologues.