Enantioselective Oxidation of Thioanisole to Metyl Phenyl Sulfoxide by Chiral Compounds Bearing N-Cl Bond

GRAPHICAL ABSTRACT

Abstract

Chiral sulfoxides are used in asymmetric synthesis and are present in various biologically active compounds. Asymmetric synthesis of the sulfoxides has been performed by chiral metal complexes and non-metals containing peroxide and oxide moieties. In this study, a new metal free method has been developed to oxidize thioanisole into methyl phenyl sulfoxide with easily accessible chiral compounds carrying N-Cl bond. For this purpose, chiral amine and amide bearing reagents were synthesized and chlorinated by using N-chlorosuccinimide. In oxidation reactions, chiral information has been transferred from N-chloramines to sulfides. With chlorinated chiral reagents, we observed enantioenriched sulfoxide formation. Although the observed results are promising, the best chiral amines are yet to be found. This is the first report on such a reaction, to the best of our knowledge.

Keywords:

• Asymmetric oxidation
• chiral sulfoxides
• chiral N-chloramines
• chiral N-chloramides