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

• Published in: Journal of molecular catalysis. A, Chemical Chemical, 2013-04, Vol.370, p.75-79
• Main Authors: Srour, Hassan, Jalkh, Joanna, Le Maux, Paul, Chevance, Soizic, Kobeissi, Marwan, Simonneaux, Gérard
• Format: Article
• Language: English
• Subjects: Asymmetric oxidation; Catalysis; Catalytic sulfoxidation; Chemical Sciences; Chemistry; Exact sciences and technology; General and physical chemistry; Hydrogen peroxide; Organic chemistry; Sulindac; Theory of reactions, general kinetics. Catalysis. Nomenclature, chemical documentation, computer chemistry; Water-soluble manganese porphyrin
• ISSN: 1381-1169; 1873-314X
• DOI: 10.1016/j.molcata.2012.12.016

[Display omitted] ► 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. 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.