title: Asymmetric syntheses of three-membered heterocycles using chiral amide-based ammonium ylides.
abstract: The use of carbonyl-stabilised ammonium ylides to access chiral glycidic amides and the corresponding aziridines has so far been limited to racemic trans-selective protocols. We herein report the development of an asymmetric approach to access such compounds with high levels of stereoselectivity using easily accessible chiral auxiliary-based ammonium ylides. The use of phenylglycinol as the chiral auxiliary was found to be superior to Evans or pseudoephedrine-based auxiliaries resulting in good to excellent stereoselectivities in both, epoxidation and aziridination reactions.
authors.affiliation: Institute of Organic Chemistry, Johannes Kepler University Linz, Altenbergerstraße 69, 4040 Linz, Austria. Mario.waser@jku.at.
authors.forename: Mathias
authors.initials: M
authors.lastname: Pichler
authors.forename: Johanna
authors.initials: J
authors.lastname: Novacek
authors.forename: Raphaël
authors.initials: R
authors.lastname: Robiette
authors.forename: Vanessa
authors.initials: V
authors.lastname: Poscher
authors.forename: Markus
authors.initials: M
authors.lastname: Himmelsbach
authors.forename: Uwe
authors.initials: U
authors.lastname: Monkowius
authors.forename: Norbert
authors.initials: N
authors.lastname: Müller
authors.forename: Mario
authors.initials: M
authors.lastname: Waser