On the mechanism of the organocatalytic asymmetric epoxidation of α,β-unsaturated aldehydes.

Mechanistic studies on the organocatalytic epoxidation of α,β-unsaturated aldehydes explore the autoinductive behavior of the reaction and establish that the hydrate/peroxyhydrate of the product is acting as a phase-transfer catalyst. Based on these studies, an improved methodology that provides high selectivities and decreased catalyst loading, through the addition of chloral hydrate, is developed.