Synthesis and reactivity of β-sulfonylvinylselenonium salts: a simple stereoselective synthesis of β-functionalized (Z)-vinyl sulfones

Abstract

The treatment of alkynylselenonium salt with benzenesulfinic acid in ⁱPrOH gives (Z)-β-sulfonylvinylselenonium salts in good yields. The alkenylselenonium salts thus prepared react with nucleophiles such as alkoxides, halides, and acetylides to produce β-functionalized (Z)-vinyl sulfones in high yields. Furthermore, we succeeded in the simple stereoselective one-step synthesis of various chiral (Z)-β-alkoxyvinyl sulfones by the use of chiral alcohols.