title: Highly enantioselective aza-Diels-Alder reaction of 1-azadienes with enecarbamates catalyzed by chiral phosphoric acids.
abstract: On demand: A highly enantio- and diastereoselective synthesis of 6-amino- trisubstituted tetrahydropyridine compounds has been developed through the inverse-electron-demand aza-Diels-Alder reaction of N-aryl α,β-unsaturated ketimines with enecarbamates (E)-1. Chiral phosphoric acid catalysts achieve simultaneous activation of both the 1-azadiene and dienophile partners.
authors.affiliation: Centre de Recherche de Gif, Institut de Chimie des Substances Naturelles, CNRS, 91198 Gif-sur-Yvette Cedex (France).
authors.forename: Long
authors.initials: L
authors.lastname: He
authors.forename: Gregory
authors.initials: G
authors.lastname: Laurent
authors.forename: Pascal
authors.initials: P
authors.lastname: Retailleau
authors.forename: Benoît
authors.initials: B
authors.lastname: Folléas
authors.forename: Jean-Louis
authors.initials: JL
authors.lastname: Brayer
authors.forename: Géraldine
authors.initials: G
authors.lastname: Masson
mesh_terms: D001372:Aza Compounds / Q000737:chemistry*; D002219:Carbamates / Q000737:chemistry*; D002384:Catalysis; D015394:Molecular Structure; D010756:Phosphoric Acids / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D001372:Aza Compounds; D002219:Carbamates; D010756:Phosphoric Acids; C030242:phosphoric acid
keywords: cycloaddition; dienes; heterocycles; organocatalysis; synthetic methods