Organomediated Enantioselective (18)F Fluorination for PET Applications

Angew Chem Int Ed Engl. 2015 Nov 2;54(45):13366-9. doi: 10.1002/anie.201506035. Epub 2015 Sep 11.

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.

Keywords: asymmetric synthesis; enamines; fluorine-18; organocatalysis; positron emission tomography.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Fluorine Radioisotopes / chemistry*
  • Glutamates / chemical synthesis*
  • Glutamates / chemistry
  • Halogenation*
  • Molecular Structure
  • Positron-Emission Tomography*
  • Stereoisomerism

Substances

  • Fluorine Radioisotopes
  • Glutamates
  • 4-fluoroglutamic acid