title: Enantioselective synthesis and stereoselective ring opening of N-acylaziridines.
abstract: Kinetic resolution of N-acylaziridines by nucleophilic ring opening was achieved with (R)-BINOL as the chiral modifier under boron-catalyzed conditions (see scheme; Ar=3,5-dinitrophenyl). The consumed enantiomer of aziridine can be further converted to an enantioenriched 1,2-chloroamide with recovery of (R)-BINOL.
authors.affiliation: Department of Chemistry and Biochemistry, University of North Carolina Wilmington, Wilmington, NC 28403, USA.
authors.forename: Jennifer
authors.initials: J
authors.lastname: Cockrell
authors.forename: Christopher
authors.initials: C
authors.lastname: Wilhelmsen
authors.forename: Heather
authors.initials: H
authors.lastname: Rubin
authors.forename: Allen
authors.initials: A
authors.lastname: Martin
authors.forename: Jeremy B
authors.initials: JB
authors.lastname: Morgan
mesh_terms: D001388:Aziridines / Q000138:chemical synthesis* / Q000737:chemistry; D001895:Boron / Q000737:chemistry; D002384:Catalysis; D007700:Kinetics; D009284:Naphthols / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D001388:Aziridines; C406944:BINOL, naphthol; D009284:Naphthols; C033132:aziridine; D001895:Boron