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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.

Original publication

DOI

10.1002/anie.201506035

Type

Journal article

Journal

Angew Chem Int Ed Engl

Publication Date

02/11/2015

Volume

54

Pages

13366 - 13369

Keywords

asymmetric synthesis, enamines, fluorine-18, organocatalysis, positron emission tomography, Fluorine Radioisotopes, Glutamates, Halogenation, Molecular Structure, Positron-Emission Tomography, Stereoisomerism