Organomediated Enantioselective 18F Fluorination for PET Applications
Faye Buckingham
University of Oxford, Chemistry Research Laboratory, 12 Mansfield Road, Oxford, OX1 3TA (UK)
Search for more papers by this authorDr. Anna K. Kirjavainen
Turku PET Centre, Radiopharmaceutical Chemistry Laboratory, Kiinamyllynkatu 4–8, 20520 Turku (Finland)
Search for more papers by this authorDr. Sarita Forsback
Turku PET Centre, Radiopharmaceutical Chemistry Laboratory, Kiinamyllynkatu 4–8, 20520 Turku (Finland)
Search for more papers by this authorAnna Krzyczmonik
Turku PET Centre, Radiopharmaceutical Chemistry Laboratory, Kiinamyllynkatu 4–8, 20520 Turku (Finland)
Search for more papers by this authorThomas Keller
Turku PET Centre, Radiopharmaceutical Chemistry Laboratory, Kiinamyllynkatu 4–8, 20520 Turku (Finland)
Search for more papers by this authorDr. Ian M. Newington
GE Healthcare, The Grove Centre, White Lion Road, Amersham, HP7 9LL (UK)
Search for more papers by this authorDr. Matthias Glaser
GE Healthcare, The Grove Centre, White Lion Road, Amersham, HP7 9LL (UK)
Search for more papers by this authorDr. Sajinder K. Luthra
GE Healthcare, The Grove Centre, White Lion Road, Amersham, HP7 9LL (UK)
Search for more papers by this authorProf. Olof Solin
Turku PET Centre, Radiopharmaceutical Chemistry Laboratory, Kiinamyllynkatu 4–8, 20520 Turku (Finland)
Search for more papers by this authorCorresponding Author
Prof. Véronique Gouverneur
University of Oxford, Chemistry Research Laboratory, 12 Mansfield Road, Oxford, OX1 3TA (UK)
University of Oxford, Chemistry Research Laboratory, 12 Mansfield Road, Oxford, OX1 3TA (UK)Search for more papers by this authorFaye Buckingham
University of Oxford, Chemistry Research Laboratory, 12 Mansfield Road, Oxford, OX1 3TA (UK)
Search for more papers by this authorDr. Anna K. Kirjavainen
Turku PET Centre, Radiopharmaceutical Chemistry Laboratory, Kiinamyllynkatu 4–8, 20520 Turku (Finland)
Search for more papers by this authorDr. Sarita Forsback
Turku PET Centre, Radiopharmaceutical Chemistry Laboratory, Kiinamyllynkatu 4–8, 20520 Turku (Finland)
Search for more papers by this authorAnna Krzyczmonik
Turku PET Centre, Radiopharmaceutical Chemistry Laboratory, Kiinamyllynkatu 4–8, 20520 Turku (Finland)
Search for more papers by this authorThomas Keller
Turku PET Centre, Radiopharmaceutical Chemistry Laboratory, Kiinamyllynkatu 4–8, 20520 Turku (Finland)
Search for more papers by this authorDr. Ian M. Newington
GE Healthcare, The Grove Centre, White Lion Road, Amersham, HP7 9LL (UK)
Search for more papers by this authorDr. Matthias Glaser
GE Healthcare, The Grove Centre, White Lion Road, Amersham, HP7 9LL (UK)
Search for more papers by this authorDr. Sajinder K. Luthra
GE Healthcare, The Grove Centre, White Lion Road, Amersham, HP7 9LL (UK)
Search for more papers by this authorProf. Olof Solin
Turku PET Centre, Radiopharmaceutical Chemistry Laboratory, Kiinamyllynkatu 4–8, 20520 Turku (Finland)
Search for more papers by this authorCorresponding Author
Prof. Véronique Gouverneur
University of Oxford, Chemistry Research Laboratory, 12 Mansfield Road, Oxford, OX1 3TA (UK)
University of Oxford, Chemistry Research Laboratory, 12 Mansfield Road, Oxford, OX1 3TA (UK)Search for more papers by this authorGraphical Abstract
PET molecules: A metal-free asymmetric 18F-labeling reaction for an aliphatic CH bond, employing a chiral imidazolidinone as the organomediator and N-[18F]fluorobenzenesulfonimide ([18F]NFSI) as the 18F source, is reported. The method is used to prepare the 18F-labeled positron emission tomography (PET) radiotracer (2S,4S)-4-[18F]fluoroglutamic acid.
Abstract
The first organomediated asymmetric 18F fluorination has been accomplished using a chiral imidazolidinone and [18F]N-fluorobenzenesulfonimide. The method provides access to enantioenriched 18F-labeled α-fluoroaldehydes (>90 % ee), which are versatile chiral 18F 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-[18F]fluoroglutamic acid.
Supporting Information
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