Chiral non-racemic dihydroxysulfones via hydrolytic kinetic resolutions—synthesis of oxacyclic ring systems using intramolecular acylation strategies

A number of chiral non-racemic 1,2-dihydroxysulfones have been prepared in good yields and high enantiomeric excesses by hydrolytic kinetic resolution of the corresponding epoxysulfones with Jacobsenʹs (S,S)-salen(Co)III(OAc) catalyst. The intramolecular cyclization reactions of the acyl and ethoxycarbonyl derivatives of these dihydroxysulfones have been exploited to access a variety of functionalized chiral non-racemic cyclic ethers and lactones in good yields.