What is sharpless epoxidation?

Sharpless epoxidation is a widely used organic reaction for the stereoselective synthesis of epoxides. It was developed by Nobel Prize-winning chemist Barry Sharpless in the 1980s.

The reaction involves the oxidation of an alkene with a peroxide catalyst and a chiral auxiliary to produce an epoxide. The chiral auxiliary helps to control the stereochemistry of the epoxide, resulting in high levels of stereoselectivity.

Sharpless epoxidation is commonly used in the synthesis of complex molecules, such as natural products and pharmaceuticals, where the stereochemistry of the epoxide is crucial for the desired biological activity.

The reaction is typically carried out using the catalyst titanium tetraisopropoxide and a chiral ligand, such as diethyl tartrate or tert-butyl hydroperoxide. The reaction conditions are mild and the yields are generally high, making it a versatile and useful method for the synthesis of chiral epoxides.