title: On the origin of the stereoselectivity in chiral amide-based ammonium ylide-mediated epoxidations.
abstract: Detailed DFT studies provide an in-depth mechanistic understanding for the use of chiral amide-based ammonium ylides in epoxidation reactions. It is shown that the used chiral auxiliary efficiently shields one face of the ylide, which thus results in an extraordinarily high stereoselectivity giving only one trans-isomer with perfect control of the absolute configuration.
authors.affiliation: Institute of Organic Chemistry, Johannes Kepler University Linz, Altenbergerstraße 69, 4040 Linz, Austria.
authors.forename: Johanna
authors.initials: J
authors.lastname: Novacek
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.identifier: 0000-0002-8421-8642
authors.initials: M
authors.lastname: Waser
keywords: Absolute configuration; Auxiliaries; DFT calculations; Mechanistic studies