Palladium-catalyzed domino carbopalladation/5-exo-allylic amination of alpha-amino allenamides: an efficient entry to enantiopure imidazolidinones.
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.
Beccalli
Egle M
EM
Istituto di Chimica Organica "A. Marchesini", Facolta di Farmacia, Universita di Milano, via Venezian 21, 20133 Milano, Italy.
Broggini
Gianluigi
G
Clerici
Francesca
F
Galli
Simona
S
Kammerer
Claire
C
Rigamonti
Micol
M
Sottocornola
Silvia
S
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
D000498:Allyl Compounds; D007093:Imidazoles; D010165:Palladium