Rhodium-Catalyzed Enantioselective Nucleophilic Fluorination: Ring Opening of Oxabicyclic Alkenes


  • We gratefully thank the NSERC, Merck Frosst, and Merck for an Industrial Research Chair. We also thank the University of Toronto for support of our program, Dr. Alan Lough (Chemistry Department, University of Toronto) for single-crystal X-ray structure analysis, and Solvias AG for the generous gift of chiral ligands. J.Z. thanks SIOC for a postdoctoral fellowship. G.C.T. thanks NSERC for a postgraduate scholarship.


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Done with 'F'lair: Enantioselective fluorination was achieved by RhI-catalyzed ring opening of oxabicyclic alkenes using Et3N⋅3 HF. The chiral fluorinated scaffolds were obtained under mild reaction conditions in standard glass vessels, and served as useful building blocks for various chiral fluorinated targets. cod=cycloocta-1,5-diene, ppf=phenylphosphinoferrocene, THF=tetrahydrofuran.