1126650-55-2Relevant academic research and scientific papers
Hydrogen Bonding Phase-Transfer Catalysis with Ionic Reactants: Enantioselective Synthesis of γ-Fluoroamines
Roagna, Giulia,Ascough, David M. H.,Ibba, Francesco,Vicini, Anna Chiara,Fontana, Alberto,Christensen, Kirsten E.,Peschiulli, Aldo,Oehlrich, Daniel,Misale, Antonio,Trabanco, Andrés A.,Paton, Robert S.,Pupo, Gabriele,Gouverneur, Véronique
supporting information, p. 14045 - 14051 (2020/09/16)
Ammonium salts are used as phase-Transfer catalysts for fluorination with alkali metal fluorides. We now demonstrate that these organic salts, specifically azetidinium triflates, are suitable substrates for enantioselective ring opening with CsF and a chiral bis-urea catalyst. This process, which highlights the ability of hydrogen bonding phase-Transfer catalysts to couple two ionic reactants, affords enantioenriched γ-fluoroamines in high yields. Mechanistic studies underline the role of the catalyst for phase-Transfer, and computed transition state structures account for the enantioconvergence observed for mixtures of achiral azetidinium diastereomers. The N-substituents in the electrophile influence the reactivity, but the configuration at nitrogen is unimportant for the enantioselectivity.
Synthesis of l-Boc-3-fluoroazetidine-3-carboxylic acid
Van Hende, Eva,Verniest, Guido,Deroose, Frederik,Thuring, Jan-Willem,Macdonald, Gregor,De Kimpe, Norbert
supporting information; experimental part, p. 2250 - 2253 (2009/08/07)
Synthetic strategies toward 3-fluoroazetidine-3-carboxylic acid, a new cyclic fluorinated β-amino acid with high potential as building block in medicinal chemistry, were evaluated. The successful pathway includes the bromoflu-orination of N-(diphenylmethy
