The chapter describes the development of asymmetric epoxidation catalysis, starting from the ground-breaking Sharpless asymmetric epoxidation of allylic alcohols through the Mn(salen) type Jacobsen-Katsuki epoxidation until the most recent advances focused on achieving greener and environmentally more sustainable catalytic technologies. These encompass Yamamoto's bis-hydroxamic acid catalysts as well as amine pyridine and Katsuki systems for the use of O2 and H2O2 as benign terminal oxidants. In a second part, the progress of thioether sulfoxidation starting from Kagan's protocol and its variations to the very general and efficient Bolm systems based on vanadyl and tridentate Schiff base ligands are described. Recent advances in the use of O2 for sulfoxidation are also mentioned. Mechanistic insights are presented throughout and examples regarding applications of these types of asymmetric oxidation to the synthesis of enantiomerically pure pharmaceuticals are provided.