Three-Component Reaction of Cyclopropanols, DABSO,\nand <i>N</i>‑(Sulfonyl)acrylamides: Preparation of\nSulfone-Bridged 1,7-Dicarbonyl Compounds

A cascade\nreaction of cyclopropyl alcohols, DABSO (1,4-diazoniabicyclo[2.2.2]octane-1,4-disulfinate),\nand <i>N</i>-(sulfonyl)acrylamides has been developed. This\ntandem process went through a cyclopropanol ring opening and Michael\naddition sequence. The γ-keto sulfinate generated from the reaction\nbetween cyclopropanol and DABSO serves as the nucleophilic reagent,\nand <i>N</i>-(sulfonyl)acrylamide is used as the Michael\naddition acceptor. By utilizing this strategy, multitudinous sulfone-bridged\n1,7-dicarbonyl compounds that contain both a β-sulfonyl amide\nunit and γ-keto sulfone skeleton were conveniently synthesized.