Enantioselective Catalysis

Sharpless Asymmetric Epoxidation of Allylic Alcohols

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The first of Sharpless's reactions is the oxidation of an alkene by asymmetric epoxidation. By adding a chiral ligand to the titanium catalyst the reaction becomes asymmetric. The ligand that works best is L-(+)-diethyl tartrate. The active complex is believed to be two titanium atoms bridged by two tartrate ligands. Methyl esters have been used in the animation for simplicity.