Stereoselective epoxidation of asymmetrized 2-alkenyl-1,3-propanediols

Article abstract of DOI:10.1016/0040-4039(91)80450-K

Asymmetrized 2-alkenyl 1,3-propanediols are stereoselectively epoxidized to the same main diastereoisomer both with 3-chloroperbenzoic acid and the VO(acac)₂/t-butyl hydroperoxyde system. Using the latter epoxidating reagent in combination with a protection-deprotection sequence involving the two homoallylic hydroxy groups, all the four cis epoxides were easily achieved in stereoisomeric pure from starting from a single common (Z) precursor.