Mg-Promoted Stereoselective Desulfonation of β-Arylvinyl Sulfone Derivatives

Abstract β-Arylvinyl p-tolylsulfones, easily prepared from base-catalyzed condensation of aromatic aldehydes with a variety of p-tolylsulfones, were efficiently transformed to the corresponding (E)-β-substituted aromatic olefins in a stereoselective manner through Mg-promoted reduction. The reaction may be initiated through electron transfer from Mg metal to the vinyl sulfones to give the corresponding anionic species followed by stereoselective elimination of a sulfonyl group.