title: Nucleophilic Dearomatization of Pyridines under Enamine Catalysis: Regio-, Diastereo-, and Enantioselective Addition of Aldehydes to Activated N-Alkylpyridinium Salts.
abstract: Catalytic addition of chiral enamines to azinium salts is a powerful tool for the synthesis of enantioenriched heterocycles. An unprecedented asymmetric dearomative addition of aldehydes to activated N-alkylpyridinium salts is presented. The process exhibits complete C-4 regioselectivity along with high levels of diastereo- and enantiocontrol, achieving a high-yielding synthesis of a broad range of optically active 1,4-dihydropyridines. Moreover, the presented methodology enables the synthesis of functionalized octahydropyrrolo[2,3-c]pyridines, the core structure of anticancer peptidomimetics.
authors.affiliation: Department of Industrial Chemistry "Toso Montanari" and INSTM RU Bologna, Alma Mater Studiorum-University of Bologna , Via Risorgimento 4, 40136 Bologna, Italy.
authors.forename: Giulio
authors.initials: G
authors.lastname: Bertuzzi
authors.affiliation: Department of Industrial Chemistry "Toso Montanari" and INSTM RU Bologna, Alma Mater Studiorum-University of Bologna , Via Risorgimento 4, 40136 Bologna, Italy.
authors.forename: Alessandro
authors.initials: A
authors.lastname: Sinisi
authors.affiliation: Department of Industrial Chemistry "Toso Montanari" and INSTM RU Bologna, Alma Mater Studiorum-University of Bologna , Via Risorgimento 4, 40136 Bologna, Italy.
authors.forename: Daniel
authors.initials: D
authors.lastname: Pecorari
authors.affiliation: Department of Industrial Chemistry "Toso Montanari" and INSTM RU Bologna, Alma Mater Studiorum-University of Bologna , Via Risorgimento 4, 40136 Bologna, Italy.
authors.forename: Lorenzo
authors.initials: L
authors.lastname: Caruana
authors.affiliation: Department of Industrial Chemistry "Toso Montanari" and INSTM RU Bologna, Alma Mater Studiorum-University of Bologna , Via Risorgimento 4, 40136 Bologna, Italy.
authors.forename: Andrea
authors.initials: A
authors.lastname: Mazzanti
authors.affiliation: Department of Industrial Chemistry "Toso Montanari" and INSTM RU Bologna, Alma Mater Studiorum-University of Bologna , Via Risorgimento 4, 40136 Bologna, Italy.
authors.forename: Luca
authors.identifier: 0000-0002-7840-3200
authors.initials: L
authors.lastname: Bernardi
authors.affiliation: Department of Industrial Chemistry "Toso Montanari" and INSTM RU Bologna, Alma Mater Studiorum-University of Bologna , Via Risorgimento 4, 40136 Bologna, Italy.
authors.forename: Mariafrancesca
authors.identifier: 0000-0001-9124-3304
authors.initials: M
authors.lastname: Fochi