Allenamides of α-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.
Palladium-Catalyzed Domino Carbopalladation/5-exo-Allylic amination of alfa -Amino Allenamides : an efficient entry to enantiopure imidazolidinones / E.M. Beccalli, G. Broggini, F. Clerici, S. Galli, C. Kammerer, M. Rigamonti, S. Sottocornola. - In: ORGANIC LETTERS. - ISSN 1523-7060. - 11:7(2009), pp. 1563-1566.
Palladium-Catalyzed Domino Carbopalladation/5-exo-Allylic amination of alfa -Amino Allenamides : an efficient entry to enantiopure imidazolidinones
E.M. BeccalliPrimo
;F. Clerici;
2009
Abstract
Allenamides of α-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.Pubblicazioni consigliate
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