The Enantioselective Conversion of Three-Membered Ring Sulfoxides (Episulfoxides) into Alkenyl Sulfoxides using Chiral Lithium Amide Bases

Article abstract of DOI:10.1055/s-1997-948

A novel type of chiral lithium amide base reaction, involving the rearrangement of certain types of symmetrical ring-fused episulfoxides, gives alkenyl sulfoxide products in up to 88% ee. The structure of one product, including its absolute stereochemistry, was determined by X-ray crystallography, following oxidation of the sulfoxide to the corresponding alkenyl sulfone.