Synthesis of the Smallest Axially Chiral Molecule by Asymmetric Carbon–Fluorine Bond Activation


  • D.L. and M.F.K. thank the Deutsche Forschungsgemeinschaft (DFG) for financial support within the graduate school program GRK 1582/1 “Fluor als Schlüsselelement”. M.F.K. in grateful to the AG Fluorchemie at GDCh for a conference scholarship. S.R. thanks the Fonds der Chemischen Industrie and the DFG for financial support. S.R. and T.S. thank the BWGrid for providing computational resources. This work was supported by the Ministerio de Ciencia e Innovación (MICINN) of Spain (project CTQ2009-10098) and by the Junta de Andalucía (project PO9-4708). B.N.-O. thanks MICINN for a personal doctoral grant (FPU-AP2009-2797).


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Enantioselect-DeFluor: Carbon–fluorine bond cleavage by a chiral zirconium complex allows the synthesis of optically active 1,3-difluoroallene for the first time. Its absolute configuration was established by gas-phase vibrational circular dichroism spectroscopy (see picture).