The iridium catalyzed fluorination with Et3N.3HF, employing allylic trichloroacetimidate as the electrophile allows for the formation of enantioenriched fluoride products via dynamic kinetic asymmetric transformation (DYKAT). This method provides a facile route to prepare a variety of α-linear, α-branching, and β-heteroatom substituted allylic fluorides and β-fluoroamines in good yields with excellent branched-to-linear ratios and high levels of asymmetric induction. Excellent levels of catalyst-controlled diastereoselectivities using either (R,R) or (S,S)-bicyclo[3.3.0]octadiene ligand are observed. The synthetic utility of the fluorination process is illustrated in the asymmetric synthesis of 15-fluorinated prostaglandin and neuroprotective agent P7C3-A20.

Enantioselective synthesis of allylic fluorides via iridium-catalyzed dynamic kinetic asymmetric transformations of racemic allylic trichloroacetimidates with Et3N.3HF

255th National Meeting (2018)

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