title: Phosphine-catalyzed Heine reaction.
abstract: Aziridines are important synthetic intermediates which readily undergo ring-opening reactions. It is demonstrated that electron-rich phosphines are efficient catalysts for the regioselective rearrangement of N-acylaziridines to oxazolines. The reactions occur in excellent yield under neutral conditions. Evidence is provided for an addition/elimination mechanism by generation of a phosphonium intermediate. Similar intermediates may be useful for the development of alternate aziridine ring-opening processes and stereoselective synthesis with enantiopure phosphines.
authors.affiliation: Department of Chemistry and Biochemistry, University of North Carolina Wilmington, Dobo Hall, Wilmington, North Carolina 28403, USA.
authors.forename: Allen
authors.initials: A
authors.lastname: Martin
authors.forename: Kathleen
authors.initials: K
authors.lastname: Casto
authors.forename: William
authors.initials: W
authors.lastname: Morris
authors.forename: Jeremy B
authors.initials: JB
authors.lastname: Morgan