Shi epoxidation

Overview

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.[3][4]

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