Abstract Conditions were developed for the selective epoxidation of the double bond of methyl ricinoleate (1) with ethylmethyldioxirane (EMDO) to give the homoallylic epoxyalcohol, methyl (Z)-9, 10-oxido-12-hydroxyoctadecanoate (2) in high yields but in poor enantiomeric excess. The diastereomeric ratio for epoxyalcohol 2 was improved modestly when t-butyl-hydroperoxide, coupled with a titanium catalyst and ad-tartrate ligand, was ...
