Synthesis and oxidation reactions of cycloheptatrienyl sulfones

Inexpensive cycloheptatriene is regiospecifically converted to all three phenylsulfonyl substituted cycloheptatrienes. Epoxidation of these materials with achiral reagents is shown to be relatively regiospecific. Reasonable levels of enantiomeric excess (∼63,78%) are achieved by Sharpless asymmetric dihydroxylation of a pair of 3-substituted trienes. Crystallization of these sulfones provides the diols in enantiomeric excesses greater than 90%.