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?
Side note:K. Barry Sharpless figured this puzzle out in 1980, receiving a Nobel Prize in 2001. Go science!
Important Reagents of Sharpless Epoxidation.
Diethyl tartartes (DET) of different optical activities are used to convert allyl alcohols into stereospecific epoxides.
General reaction of Sharpless Epoxidation.
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.