RESUMO
A new palladium-catalyzed synthesis of 3-amido-substituted beta-lactams is reported. This process involves the one-pot coupling of four components, imines, carbon monoxide, and acid chloride, providing a flexible route to construct this class of heterocycle. The generation of beta-lactams with two different imines can also be accomplished, providing a method to assemble these products with independent control over five separate substituents.
Assuntos
Monóxido de Carbono/química , Cloretos/química , Iminas/química , Paládio/química , beta-Lactamas/síntese química , Catálise , Estrutura MolecularRESUMO
A new palladium-catalyzed route to prepare 1,3-oxazolium-5-oxides (i.e., Münchnones) directly from imine, carbon monoxide, and acid chloride building blocks has been developed. This provides a straightforward catalytic synthesis of Münchnones and is amenable to generating a diverse range of products by simple modification of the imine or acid chloride starting materials. Münchnones are vital synthetic intermediates to a variety of heterocyclic and peptide-based molecules. As such, this methodology has been utilized to design a new catalytic synthesis of alpha-amino acid derivatives via a one-pot coupling of imines, carbon monoxide, and acid chloride followed by alcohol. The latter represents the first reported catalytic synthesis of alpha-amino acids directly from imine and carbon monoxide building blocks.
Assuntos
Aminoácidos/síntese química , Oxazóis/química , Óxidos/química , Catálise , Paládio/químicaRESUMO
One of the most facile routes to prepare carboxylate-substituted imidazolines is by the palladium-catalyzed coupling of an imine, carbon monoxide, and an acid chloride. In this reaction, a peptide unit is constructed and directly incorporated into the heterocyclic core.