title: Towards a General Understanding of Carbonyl-Stabilised Ammonium Ylide-Mediated Epoxidation Reactions.
abstract: The key factors for carbonyl-stabilised ammonium ylide-mediated epoxidation reactions were systematically investigated by experimental and computational means and the hereby obtained energy profiles provide explanations for the observed experimental results. In addition, we were able to identify the first tertiary amine-based chiral auxiliary that allows for high enantioselectivities and high yields for such epoxidation reactions.
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 Organic Chemistry, Johannes Kepler University Linz, Altenbergerstrasse 69, 4040, Linz, Austria.
authors.forename: Lukas
authors.initials: L
authors.lastname: Roiser
authors.affiliation: Institute of Organic Chemistry, Johannes Kepler University Linz, Altenbergerstrasse 69, 4040, Linz, Austria.
authors.forename: Katharina
authors.initials: K
authors.lastname: Zielke
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. raphael.robiette@uclouvain.be.
authors.forename: Raphaël
authors.initials: R
authors.lastname: Robiette
authors.affiliation: Institute of Organic Chemistry, Johannes Kepler University Linz, Altenbergerstrasse 69, 4040, Linz, Austria. mario.waser@jku.at.
authors.forename: Mario
authors.initials: M
authors.lastname: Waser
keywords: chiral auxiliary; density functional calculations; diastereoselectivity; enantioselectivity; ylides