Allylic 4-Methoxybenzoates display excellent Reagent-controlled double diastereoselection in the sharpless asymmetric dihydroxylation: Application to highly selective total syntheses of polyols

Article abstract of DOI:10.1016/S0040-4039(97)01327-0

The asymmetric dihydroxylation of several enantiomerically pure 4-substituted allylic 4-methoxybenzoates proceeds with excellent reagent-controlled diastereoselectivities. This observation, coupled with the high enantio- and regioselectivity provided by the Sharpless asymmetric dihydroxylation of suitably protected dienes, has been used to accomplish the stereocontrolled total syntheses of several vic-polyols.