Oxidation Kinetics Resolution of Racemic Aromatic Sulfoxides by Chiral Porphyrin-Inspired N4 Ligand with Manganese Complex

Oxidative kinetics resolution of racemic aromatic sulfoxide was studied by using chiral porphyrin-inspired N-4 ligands and manganese in situ complex as catalyst, environment-friendly H2O2 as oxidant and adamantanecarboxvlic acid as additive. The arylalkyl and arylbenzyl sulfoxide substrates were extended by this catalytic system. A maximum Yield of chiral sulfoxide was 40% and the enantioselectivity was 100%. In the meantime, the yield of sulfone a further oxidation products of sulfoxide, was up to 72%. It was found that the catalytic oxidation system is more prone to electron-rich sulfoxide through the competition experiment between electron-rich sulfoxide and electron-deficient sulfoxide substrates. In addition, the success of gram-scale oxidation kinetic resolution also shows that this method has a certain practical value in methodology