Studies on the Stereochemistry in the Alkylation of Enolate Ion of Cyclic β-Keto Ester with Sulfonium Salts Containing Optically Active Alkyl Groups

Article abstract of DOI:10.1246/cl.1987.327

Alkylation of cyclic β-keto ester with racemic sulfonium salts containing optically active alkyl groups such as (S)-2-octyl and (S)-2-butyl was found to afford C-alkylated products with inversion of configuration at asymmetric alkyl carbon atom.Stereochemical reaction course via formation of S-O sulfurane intermediate and succesive stereoselective intramolecular alkyl migration to enolate is described.