ChemInform Abstract: syn Stereocontrol in the Directed Dihydroxylation of Acyclic Allylic Alcohols

The preparation and directed dihydroxylation of a series of acyclic allylic alcohols is reported. The oxidation reaction is capable of demonstrating high levels of diastereoselection for the syn isomer. An explanation of the observed selectivities based on the degree of allylic strain is presented and a transition state model proposed.