Shi epoxidation
Named reactionOxidation
The Shi epoxidation is a chemical reaction, as the asymmetric epoxidation of alkenes with oxone (potassium peroxymonosulfate) and a fructose-derived catalyst (1). This reaction is thought to proceed via a dioxirane intermediate, generated when the oxone peroxidizes the catalyst ketone. (The oxone sulfate group facilitates dioxirane formation by acting as a good leaving group during ring closure.) Its non-metal catalyst represents an early example of organocatalysis.