38353-74-1Relevant articles and documents
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
, 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.
3-aminoazetidine, its salts and intermediates of synthesis
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, (2008/06/13)
The 3-aminoazetidine, its salts, new intermediates of formula STR1 wherein X' represents hydrogen or a protecting group and both X" represent hydrogen or, together with the nitrogen atom, a phthalimido group, X' not and both X" being hydrogen at the same
