Regio- and stereo-selective synthesis of β-sulphonyl-α,β-unsaturated carbonyl compounds via an iodosulphonylation–dehydroiodination reaction

Abstract

α,β-Unsaturated carbonyl compounds underwent regiospecific lodosulphonylation with toluene-p-sulphonyl iodide or sodium toluene-p-sulphinate and iodine to afford products (2), which were stereoselectively dehydroiodinated by triethylamine to give β-sulphonyl derivatives (3). The reactivity of compounds (3) as cationic β-acylvinyl equivalents, tested with amines or thiophenol, gave compounds (4) resulting from a displacement reaction.