Asymmetric Electrophilic Fluorocyclization with Carbon Nucleophiles


  • We thank AstraZeneca (J.W.), the European Union (PIEF-GA-2008-220034 to O.L), the EPSRC (J.W. and J.I.), the Skaggs-Oxford Scholarship Program, and NSF GRFP (predoctoral fellowships to K.M.E) for generous funding and Dr. Lorraine Combettes for preliminary experimentation. V.G. holds a Royal Society Wolfson Research Merit Award.


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Twist of ‘F'ate: Various helical-shaped fluorinated tetracyclic molecules were prepared by fluorocarbocyclization of prochiral alkenes. The development of a new class of chiral Selectfluor (1) proved instrumental in developing an asymmetric variant of this transformation. These novel chiral N-F reagents are readily accessible by fluorine transfer from shelf-stable N-fluoropyridinium salts.