Stereoselective Synthesis of Enantiopure 4,5-Dihydroxy-2-Alkene Esters from Simple Allylic Alcohols

Article abstract of DOI:10.1016/0040-4020(95)00554-L

A general stereoselective synthesis of 4,5-dihydroxy-2-alkene esters is developed using the photo-induced rearrangement of α,β-epoxy diazomethyl ketones.Starting with readily available enantiopure allylic alcohols that contain a chiral center at C4, i.e. a protected secondary alcohol function, a neighboring stereogenic center is introduced by irradiation of the mentioned diazo ketones.The configuration of this newly introduced center is determined by the chiral inductor used in the Sharpless epoxidation of the allylic alcohol and therefore can be selected at will.