Synthesis and oxidation reactions of cycloheptatrienyl sulfones

Inexpensive cycloheptatriene is regiospecifically converted to all three ph enylsulfonyl substituted cycloheptatrienes. Epoxidation of these materials with achiral reagents is shown to be relatively regiospecific. Reasonable l evels of enantiomeric excess (similar to 63,78%) are achieved by Sharpless asymmetric dihydroxylation of a pair of 3-substituted trienes. Crystallizat ion of these sulfones provides the diols in enantiomeric excesses greater t han 90%. (C) 2000 Published by Elsevier Science Ltd.