title: Bifunctional Ammonium Salt Catalyzed Asymmetric α-Hydroxylation of β-Ketoesters by Simultaneous Resolution of Oxaziridines.
abstract: Chiral bifunctional urea-containing ammonium salts were found to be very efficient catalysts for asymmetric α-hydroxylation reactions of β-ketoesters with oxaziridines under base-free conditions. The reaction is accompanied by a simultaneous kinetic resolution of the oxaziridine and a plausible and so far unprecedented bifunctional transition-state model has been obtained by means of DFT calculations.
authors.affiliation: Institute of Organic Chemistry, Johannes Kepler University Linz, Altenbergerstr. 69, 4040, Linz, Austria.
authors.forename: Johanna
authors.initials: J
authors.lastname: Novacek
authors.affiliation: Department of Chemistry, Binghamton University, Binghamton, New York, 13902, USA.
authors.forename: Joseph A
authors.initials: JA
authors.lastname: Izzo
authors.affiliation: Department of Chemistry, Binghamton University, Binghamton, New York, 13902, USA.
authors.forename: Mathew J
authors.initials: MJ
authors.lastname: Vetticatt
authors.affiliation: Institute of Organic Chemistry, Johannes Kepler University Linz, Altenbergerstr. 69, 4040, Linz, Austria.
authors.forename: Mario
authors.identifier: http://orcid.org/0000-0002-8421-8642
authors.initials: M
authors.lastname: Waser
keywords: asymmetric catalysis; ion pairs; non-covalent interactions; resolution; transition-state model