Sharpless Epoxidation

The Sharpless Epoxidation is the formation of a specific enantiomer of an epoxide from an alkene with titanium tetraisopropoxide as catalyst, and the chirality of the product depends on the chirality of the diethyl tartrate. The oxidizing agent is tert-butyl hydroperoxide. The epoxide can be further converted to diols, aminoalcohols, and ethers, and the formation of this chiral epoxide is an important step in forming a specific enantiomer of the subsequent products. Epoxides can be formed by other means as well, such as with peroxyacids, but these methods do not produce enantiomerically pure products. The enantioselectivity of this reactions opens the door for synthesis of specific enantiomers for pharmaceutical purposes. The chiral ligand affects the product because the ligand determines which carbon the titanium catalyst attacks first, thus determining chirality.