title: Palladium-catalyzed domino carbopalladation/5-exo-allylic amination of alpha-amino allenamides: an efficient entry to enantiopure imidazolidinones.
abstract: Allenamides of alpha-amino acids were converted into enantiopure 2-vinylimidazolidin-4-ones by a carbopalladation/exo-cyclization process. The products were obtained in 2.5:1-5.5:1 dr, with 94-99% ee. The palladium-catalyzed carbonylative cyclization of the same substrates afforded enone structures. Starting from properly substituted allenamides, an intramolecular carbopalladation followed by intramolecular amination gave rise to tricyclic fused-ring imidazolidinones.
authors.affiliation: Istituto di Chimica Organica "A. Marchesini", Facolta di Farmacia, Universita di Milano, via Venezian 21, 20133 Milano, Italy.
authors.forename: Egle M
authors.initials: EM
authors.lastname: Beccalli
authors.forename: Gianluigi
authors.initials: G
authors.lastname: Broggini
authors.forename: Francesca
authors.initials: F
authors.lastname: Clerici
authors.forename: Simona
authors.initials: S
authors.lastname: Galli
authors.forename: Claire
authors.initials: C
authors.lastname: Kammerer
authors.forename: Micol
authors.initials: M
authors.lastname: Rigamonti
authors.forename: Silvia
authors.initials: S
authors.lastname: Sottocornola
mesh_terms: D000498:Allyl Compounds / Q000737:chemistry*; D000586:Amination; D002384:Catalysis; D003500:Cyclization; D007093:Imidazoles / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D010165:Palladium / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000498:Allyl Compounds; D007093:Imidazoles; D010165:Palladium