Enantioselective radiosynthesis of positron emission tomography (PET) tracers containing [18F]fluorohydrins

Thomas J.A. Graham, R. Frederick Lambert, Karl Ploessl, Hank F. Kung, Abigail Gutmann Doyle

Research output: Contribution to journalArticle

52 Scopus citations

Abstract

Herein, we describe an operationally straightforward radiosynthesis of a chiral transition metal fluoride catalyst, [18F](salen)CoF, and its use for late-stage enantioselective aliphatic radiofluorination. We demonstrate the utility of the method by preparing single enantiomer experimental and clinically validated PET tracers that contain base-sensitive functional groups, epimerizable stereocenters, and nitrogen-rich motifs. Unlike the conventional radiosyntheses of these targets with [18F]KF, labeling with (salen)CoF is possible in the last step and under exceptionally mild conditions. These results constitute a rare example of a nucleophilic radiofluorination using a transition metal fluoride and highlight the potential of such reagents to enhance traditional methods for labeling aliphatic hydrocarbons.

Original languageEnglish (US)
Pages (from-to)5291-5294
Number of pages4
JournalJournal of the American Chemical Society
Volume136
Issue number14
DOIs
StatePublished - Apr 9 2014

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

Fingerprint Dive into the research topics of 'Enantioselective radiosynthesis of positron emission tomography (PET) tracers containing [<sup>18</sup>F]fluorohydrins'. Together they form a unique fingerprint.

  • Cite this