Electrolytic Partial Fluorination of Organic Compounds.71. Highly Diastereoselective Anodic Fluorination of Sulfides Having Oxygen-Containing Heterocyclic Groups

Diastereoselective anodic fluorination of sulfides having various oxygen-containing heterocyclic
substituents such as 2-furanyl, 1,3-dioxolanyl, 2,2-dimethyl-1,3-dioxolanyl, 2-spirocyclohexyl-1,3-dioxolanyl, 2-spiroadamantyl-1,3-dixolanyl, and 1,3-dioxolanonyl groups at the β-position was
comparatively studied. Among the oxygen-containing heterocyclic substituents, the 2-spirocyclohexyl-1,3-dioxolanyl group gave the best diastereoselectivity (80% de). The diastereoselectivity was
also affected by supporting fluoride salts and solvents. Chemical fluorination using selectfluor
resulted in much lower diastereoselectivity and extremely poor yield. The fluorinated products were
readily converted into the corresponding fluorinated diol in good yields by acidic hydrolysis.