Sharpless Epoxidation

Epoxidation of an asymmetrical alkene is usually a non-stereospecfic process, yielding a racemic mixture of enantiomers. How do you select for one enantiomer over another?

K. Barry Sharpless figured this puzzle out in 1980, receiving a Nobel Prize in 2001. Go science!

Diethyl tartartes (DET) of different optical activities are used to convert allyl alcohols into stereospecific epoxides.  

Concept: How to draw and predict a Sharpless Epoxidation.


Always draw alcohol on the bottom right corner of the double bond. Then determine which epoxide you get according to the DET used.