Co(salen)-mediated enantioselective radiofluorination of epoxides. Radiosynthesis of enantiomerically enriched [18F]F-MISO via kinetic resolution

Evgeny V. Revunov, Fedor Zhuravlev

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    Abstract

    The first example of transition metal mediated enantioselective radiofluorination of epoxides is reported. The procedure utilizes gaseous [18F]HF in a combination with (−)tetramisole and (R,R)-Co(salen), giving the corresponding (S,S)-18F-fluorohydrines in 78–93% radiochemical yield (RCY) and 20–46% enantioselectivities (ee). The use of this methodology allowed for a single step radiosynthesis of [18F]F-MISO, which took 1.5h and after solid phase-based purification delivered [18F]F-MISO in 81%/45% analytical/preparative RCY and 55% ee.
    Original languageEnglish
    JournalJournal of Fluorine Chemistry
    Volume156
    Pages (from-to)130-135
    ISSN0022-1139
    DOIs
    Publication statusPublished - 2013

    Keywords

    • Radiofluorination
    • Metal mediated
    • F-MISO
    • PET
    • [18F]

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