title: On the mechanism of the organocatalytic asymmetric epoxidation of α,β-unsaturated aldehydes.
abstract: 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.
authors.affiliation: Center for Catalysis, Department of Chemistry, Aarhus University, Langelandsgade 140, 8000 Aarhus C (Denmark), Fax: (+45) 8715-5956.
authors.forename: Rebecca L
authors.initials: RL
authors.lastname: Davis
authors.forename: Kim L
authors.initials: KL
authors.lastname: Jensen
authors.forename: Björn
authors.initials: B
authors.lastname: Gschwend
authors.forename: Karl Anker
authors.initials: KA
authors.lastname: Jørgensen
keywords: asymmetric epoxidation; organocatalysis; reaction mechanisms