A Sulfoxide Version of the Julia–Lythgoe Olefination: A New Method for the Synthesis of Olefins from Carbonyl Compounds and Sulfoxides with Carbon–Carbon Coupling

Reaction of β-mesyloxy (or acetoxy) sulfoxides, derived from alkyl (or arylmethyl) phenyl sulfoxides and carbonyl compounds in two steps, with alkylmetals (n-BuLi, t-BuLi, or EtMgBr) at low temperature gave olefins in good to excellent yields. When the β-hydroxy sulfoxides derived from arylaldehydes were treated with mesyl chloride in the presence of triethylamine, the sulfoxides directly gave E-olefins in good yields. These reactions offer a sulfoxide version of the Julia–Lythgoe olefination. The reductive vicinal elimination was found to take place through the direct sulfoxide–metal exchange. The stereochemistry of the elimination was investigated and found to be stereospecific; however, the stereospecificity was found to be dependent on the substrates.