The Sharpless epoxidation, developed by K. Barry Sharpless in 1980, has been utilized for the kinetic resolution of a racemic mixture of allylic alcohols. While extremely effective at resolving a number of allylic alcohols, this method has a number of drawbacks. Reaction times can run as long as 6 days, and the catalyst is not recyclable. However, the Sharpless asymmetric epoxidation kinetic resolution remains one of the most effective synthetic kinetic resolutions to date. A number of different tartrates can be used for the catalyst; a representative scheme is shown below utilizing diisopropyl tartrate. This method has seen general use on a number of secondary allylic alcohols.
Sharpless asymmetric dihydroxylation has also seen use as a method for kinetic resolution. This method is not widely used, however, since the same resolution can be accomplished in different manners that are more economical. Additionally, the Shi epoxidation has been shown to affect kinetic resolution of a limited selection of olefins. This method is also not widely used, but is of mechanistic interest.