title: Organomediated Enantioselective (18)F Fluorination for PET Applications.
abstract: The first organomediated asymmetric (18)F fluorination has been accomplished using a chiral imidazolidinone and [(18)F]N-fluorobenzenesulfonimide. The method provides access to enantioenriched (18)F-labeled α-fluoroaldehydes (>90% ee), which are versatile chiral (18)F synthons for the synthesis of radiotracers. The utility of this process is demonstrated with the synthesis of the PET (positron emission tomography) tracer (2S,4S)-4-[(18)F]fluoroglutamic acid.
authors.affiliation: University of Oxford, Chemistry Research Laboratory, 12 Mansfield Road, Oxford, OX1 3TA (UK).
authors.forename: Faye
authors.initials: F
authors.lastname: Buckingham
authors.affiliation: Turku PET Centre, Radiopharmaceutical Chemistry Laboratory, Kiinamyllynkatu 4-8, 20520 Turku (Finland).
authors.forename: Anna K
authors.initials: AK
authors.lastname: Kirjavainen
authors.affiliation: Turku PET Centre, Radiopharmaceutical Chemistry Laboratory, Kiinamyllynkatu 4-8, 20520 Turku (Finland).
authors.forename: Sarita
authors.initials: S
authors.lastname: Forsback
authors.affiliation: Turku PET Centre, Radiopharmaceutical Chemistry Laboratory, Kiinamyllynkatu 4-8, 20520 Turku (Finland).
authors.forename: Anna
authors.initials: A
authors.lastname: Krzyczmonik
authors.affiliation: Turku PET Centre, Radiopharmaceutical Chemistry Laboratory, Kiinamyllynkatu 4-8, 20520 Turku (Finland).
authors.forename: Thomas
authors.initials: T
authors.lastname: Keller
authors.affiliation: GE Healthcare, The Grove Centre, White Lion Road, Amersham, HP7 9LL (UK).
authors.forename: Ian M
authors.initials: IM
authors.lastname: Newington
authors.affiliation: GE Healthcare, The Grove Centre, White Lion Road, Amersham, HP7 9LL (UK).
authors.forename: Matthias
authors.initials: M
authors.lastname: Glaser
authors.affiliation: GE Healthcare, The Grove Centre, White Lion Road, Amersham, HP7 9LL (UK).
authors.forename: Sajinder K
authors.initials: SK
authors.lastname: Luthra
authors.affiliation: Turku PET Centre, Radiopharmaceutical Chemistry Laboratory, Kiinamyllynkatu 4-8, 20520 Turku (Finland).
authors.forename: Olof
authors.initials: O
authors.lastname: Solin
authors.affiliation: University of Oxford, Chemistry Research Laboratory, 12 Mansfield Road, Oxford, OX1 3TA (UK). veronique.gouverneur@chem.ox.ac.uk.
authors.forename: Véronique
authors.initials: V
authors.lastname: Gouverneur
mesh_terms: D005462:Fluorine Radioisotopes / Q000737:chemistry*; D005971:Glutamates / Q000138:chemical synthesis* / Q000737:chemistry; D054879:Halogenation; D015394:Molecular Structure; D049268:Positron-Emission Tomography; D013237:Stereoisomerism
chemical_list: D005462:Fluorine Radioisotopes; D005971:Glutamates; C038473:4-fluoroglutamic acid
keywords: asymmetric synthesis; enamines; fluorine-18; organocatalysis; positron emission tomography