Asymmetric oxidation of sulfides by hydrogen peroxide catalyzed by chiral manganese porphyrins in water/methanol solution

An efficient asymmetric oxidation of sulfides catalyzed by water-soluble chiral manganese porphyrin was carried out in presence of cheap and environmentally benign oxidant H2O2 at 25 °C. Prochiral sulfides were converted to respective sulfoxides with up to 100% conversion and up to 57% enantiomeric excess. The present study demonstrated the necessity of water as solvent and imidazole as co-catalyst. Application to the preparation of the optically drug, sulindac, was demonstrated.

Figure optionsDownload high-quality image (124 K)Download as PowerPoint slideHighlights
► We examine asymmetric oxidation of sulfides catalyzed by manganese porphyrins with H2O2.
► The necessity of water as solvent and imidazole as co-catalyst was demonstrated.
► One equivalent of hydrogen peroxide is sufficient to obtain yields up to 90–100%.
► Enantioselective synthesis of sulindac was demonstrated as an application.