title: Asymmetric fluorination of enamides: access to α-fluoroimines using an anionic chiral phase-transfer catalyst.
abstract: The use of a BINOL-derived phosphate as a chiral anionic phase-transfer catalyst in a nonpolar solvent allows the enantioselective fluorination of enamides using Selectfluor as the fluorinating reagent. We demonstrate that a wide range of stable and synthetically versatile α-(fluoro)benzoylimines can be readily accessed with high enantioselectivity. These compounds have the potential to be readily elaborated into a range of highly stereodefined β-fluoroamines, compounds that constitute highly valuable building blocks of particular importance in the synthesis of pharmaceuticals.
authors.affiliation: Department of Chemistry, University of California, Berkeley, 94720, United States.
authors.forename: Robert J
authors.initials: RJ
authors.lastname: Phipps
authors.forename: Kenichi
authors.initials: K
authors.lastname: Hiramatsu
authors.forename: F Dean
authors.initials: FD
authors.lastname: Toste
mesh_terms: D000577:Amides / Q000737:chemistry*; D002384:Catalysis; D005464:Fluorobenzenes / Q000138:chemical synthesis* / Q000737:chemistry; D054879:Halogenation; D007097:Imines / Q000138:chemical synthesis* / Q000737:chemistry; D009284:Naphthols / Q000737:chemistry*; D010710:Phosphates / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D000577:Amides; C406944:BINOL, naphthol; D005464:Fluorobenzenes; D007097:Imines; D009284:Naphthols; D010710:Phosphates