The mechanism of polyleucine catalysed asymmetric epoxidation

Abstract

Catalysis in the Juliá–Colonna epoxidation of α,β-unsaturated ketones is due to binding of the hydroperoxide enolate intermediate by the three N-terminal amidic N–H groups of α-helical poly-leucine; the N-terminal pair forms an oxy-anion hole, whilst the third aids displacement of hydroxide.