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The Enantioselective Conversion of Three-Membered Ring Sulfoxides (Episulfoxides) into Alkenyl Sulfoxides using Chiral Lithium Amide Bases
31 December 2000 (online)
A novel type of chiral lithium amide base reaction, involving the rearrangement of certain types of unsymmetrical 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.
episulfoxide - alkenyl sulfoxide - chiral lithium amide base