Exocyclic iminium salts as catalysts for alkene epoxidation by Oxoneρ

Article abstract of DOI:10.1016/S0040-4020(99)00014-9

Exocyclic iminium salts are evaluated as catalysts for alkene epoxidation by Oxone, presumed to proceed via the corresponding oxaziridinium species. Iminium triflate salts derived from pyrrolidine and electron poor aromatic aldehydes were found to be good catalysts. Attempts to prepare chiral variants of these iminium salts were largely unsuccessful, presumably due to their ready hydrolysis.