Transition Metal Catalyzed Asymmetric Oxidation of Sulfides: From Discovery to Recent Trends

In the past decades, chiral sulfoxides have been finding increasing use, reflecting a wide interest in both convenient auxiliaries in asymmetric synthesis and products with biological properties containing a chiral sulfinyl group. Since the breakthrough of the groups of Kagan and of Modena (1984) who discovered that modified titanium(IV) isopropoxide - diethyltartrate catalyst systems (known as “modified Katsuki-Sharpless reagents”) are capable of asymmetric oxidizing of prochiral sulfides by alkylhydroperoxides, plethora of modifications and practical applications of titanium based catalyst systems for the asymmetric oxidation of sulfides to sulfoxides emerged. Diverse catalysts based on titanium complexes with other chiral ligands as well as on other transition metal complexes appeared, especially in the last fifteen years. The aim of this review is to cover the progress in transition metal catalyzed asymmetric sulfides oxidations achieved since the milestone discoveries of early 1980s and to bring out the main trends of this important field of modern catalytic chemistry.