Asymmetric oxidation of sulfides with H2O2 catalyzed by titanium complexes with aminoalcohol derived Schiff bases

Sulfoxidation catalysts generated in situ from titanium(IV) isopropoxide and enantiopure Schiff bases promote the enantioselective oxidation of alkyl aryl sulfides to the corresponding sulfoxides at low catalyst loadings (<1 mol%), 30% aqueous hydrogen peroxide being the terminal oxidant. Upon screening of several ligands derived from β-aminoalcohols and salicylaldehydes, a catalyst affording sulfoxides with over 90% chemoselectivity and up to 60% ee was found, and the kinetics of the catalytic reaction was analyzed by 1H NMR.

Graphical abstractSulfoxidation catalysts generated in situ from titanium(IV) isopropoxide and enantiopure Schiff bases promote the enantioselective oxidation of alkyl aryl sulfides to the corresponding sulfoxides with over 90% chemoselectivity and up to 60% ee at low catalyst loadings (<1 mol%), 30% aqueous hydrogen peroxide being the terminal oxidant. Figure optionsDownload full-size imageDownload as PowerPoint slide