Enantioconvergent transformation of racemic cis-dialkyl substituted epoxides to (R,R) threo diols by microsomal epoxide hydrolase catalysed hydrolysis

Article abstract of DOI:10.1016/S0040-4039(96)02094-1

Both enantiomers of (±)-9,10-epoxystearic acid (1b), cis-(±)-5,6-epoxyhexadecane (1c) and cis-(±)-11,12-epoxyhexadecan-1-ol (1d) as well as the meso cis-9,10-epoxyoctadecane (1a) undergo microsomal epoxide hydrolase catalyzed hydration at the (S) carbon to give the corresponding (R,R) threo diols in a >90 e.e. Copyright (C) 1996 Elsevier Science Ltd.