title: Benzylic Ammonium Ylide Mediated Epoxidations.
abstract: A high yielding synthesis of stilbene oxides using ammonium ylides has been developed. It turned out that the amine leaving group plays a crucial role as trimethylamine gives higher yields than DABCO or quinuclidine. The amine group also influences the diastereoselectivity, and detailed DFT calculations to understand the key parameters of these reactions have been carried out.
authors.affiliation: Institute of Organic Chemistry, Johannes Kepler University Linz, Altenbergerstraße 69, 4040 Linz, Austria.
authors.forename: Lukas
authors.initials: L
authors.lastname: Roiser
authors.affiliation: Institute of Condensed Matter and Nanosciences, Université catholique de Louvain, Place Louis Pasteur 1 box L4.01.02, 1348 Louvain-la-Neuve, Belgium.
authors.forename: Raphaël
authors.initials: R
authors.lastname: Robiette
authors.affiliation: Institute of Organic Chemistry, Johannes Kepler University Linz, Altenbergerstraße 69, 4040 Linz, Austria.
authors.forename: Mario
authors.initials: M
authors.lastname: Waser
keywords: DFT calculations; diastereoselectivity; diazo compounds; epoxides; ylides