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.
Journal of Fluorine Chemistry, 2013, Vol 156, p. 130-135
Radiofluorination; Metal mediated; F-MISO; PET; [18F]