231953-54-1Relevant 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
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.
Iron catalysed cross-couplings of azetidines-application to the formal synthesis of a pharmacologically active molecule
Parmar, Dixit,Henkel, Lena,Dib, Josef,Rueping, Magnus
supporting information, p. 2111 - 2113 (2015/02/05)
A protocol for the coupling of 3-iodoazetidines with Grignard reagents in the presence of an iron catalyst has been developed. A variety of aryl, heteroaryl, vinyl and alkyl Grignards were shown to participate in the coupling process to give the products in good to excellent yields. Furthermore, a short formal synthesis towards a pharmacologically active molecule was shown. This journal is
