Regio- and Stereocontrolled Synthesis of Epoxy Alcohols and Triols from Allylic and Homoallylic Alcohols via Iodo Carbonates

Article abstract of DOI:10.1021/jo00145a004

The regio- and stereoselective synthesis of cyclic iodo carbonates 1-10, resulting from allylic and homoallylic alcohols was investigated.These useful intermediates were easily hydrolyzed to epoxy alcohols 11-20 or triols 21-30, depending on the polymeric reagent employed (Amberlyst A 26 in the OH^- or CO3^2- form, respectively).Stereochemical assignments were carried out by 13C NMR or 1H NMR correlations and by conversion of the compounds to products of known stereostructures.