Synthetic applications of 3-(phenylsulfinyl)-3-sulfolene

Article abstract of DOI:10.1002/jccs.200000009

The title compound 2 was readily prepared by MCPBA oxidation of the sulfide 1. Thermal desulfonylation of 2 gave the sulfoxide-substituted diene 3. The Diels-Alder reactions of 3 with various dienophiles gave the cyclized products 4-9 in good yields. The regiochemistry was found to be dominated by the phenylsulfinyl group, but could be reversed by the presence of a Lewis acid. Deprotonation of 2 by BuLi, followed by the reaction with alkyl halides, gave the substituted 2-sulfolenes 10. A synthetic application of 10 was demonstrated by converting 10e to the bicyclic product 11.