Hydrogen Bonding Phase-Transfer Catalysis with Ionic Reactants: Enantioselective Synthesis of γ-Fluoroamines

Giulia Roagna, David M. H. Ascough, Francesco Ibba, Anna Chiara Vicini, Alberto Fontana, Kirsten E. Christensen, Aldo Peschiulli, Daniel Oehlrich, Antonio Misale, Andrés A. Trabanco, Robert S. Paton, Gabriele Pupo* and Véronique Gouverneur*

*University of Oxford, Chemistry Research Laboratory, 12 Mansfield Road, Oxford OX1 3TA, U.K., Email: gabriele.pupochem.ox.ac.uk, veronique.gouverneurchem.ox.ac.uk

G. Roagna, D. M. H. Ascough, F. Ibba, A. C. Vicini, A. Fontana, K. E. Christensen, A. Peschiulli, D. Oehrich, A. Misale, A. A. Tranco, R. S. Paton, G. Pupo, V. Gouverneur, J. Am. Chem. Soc., 2020, 142, 14045-14051.

DOI: 10.1021/jacs.0c05131

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Abstract

Azetidinium triflates are suitable substrates for enantioselective ring opening with CsF and a chiral bis-urea catalyst. The ability of hydrogen bonding phase-transfer catalysts to couple two ionic reactants, affords enantioenriched γ-fluoroamines in high yields.

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Key Words

fluorination, azetidines, organocatalysis

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ID: J48-Y2020