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

Hassan Srour (1) , Joanna Jalkh , Paul Le Maux (1) , Soizic Chevance (1) , Marwan Kobeissi , Gérard Simonneaux (1)

1 ISCR - Institut des Sciences Chimiques de Rennes

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.

Keywords: Asymmetric oxidation; Catalytic sulfoxidation; Water-soluble manganese porphyrin; Hydrogen peroxide; Sulindac

Domains: Organic chemistry

Hassan Srour, Joanna Jalkh, Paul Le Maux, Soizic Chevance, Marwan Kobeissi, et al.. Asymmetric oxidation of sulfides by hydrogen peroxide catalyzed by chiral manganese porphyrins in water/methanol solution. Journal of Molecular Catalysis A: Chemical, 2013, 370, pp.75-79. ⟨10.1016/j.molcata.2012.12.016⟩. ⟨hal-00870853⟩