title: Synthesis of β-fluoroamines by Lewis base catalyzed hydrofluorination of aziridines.
abstract: Lewis base catalysis promotes the in situ generation of amine-HF reagents from benzoyl fluoride and a non-nucleophilic alcohol. The hydrofluorination of aziridines to provide β-fluoroamines using this latent HF source is described. This protocol displays a broad scope with respect to aziridine substitution and N-protecting groups. Examples of regio- and diastereoselective ring opening to access medicinally relevant β-fluoroamine building blocks are presented.
authors.affiliation: Department of Chemistry, Princeton University, Princeton, New Jersey 08544, USA.
authors.forename: Julia A
authors.initials: JA
authors.lastname: Kalow
authors.forename: Dana E
authors.initials: DE
authors.lastname: Schmitt
authors.forename: Abigail G
authors.initials: AG
authors.lastname: Doyle
mesh_terms: D000588:Amines / Q000737:chemistry*; D001388:Aziridines / Q000138:chemical synthesis* / Q000737:chemistry*; D002384:Catalysis; D054879:Halogenation; D058115:Lewis Bases / Q000737:chemistry*; D015394:Molecular Structure
chemical_list: D000588:Amines; D001388:Aziridines; D058115:Lewis Bases