The development of a catalytic synthesis of münchnones: a simple four-component coupling approach to alpha-amino acid derivatives.
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.
Dhawan
Rajiv
R
Department of Chemistry, McGill University, 801 Sherbrooke Street West, Montreal, Quebec H3A 2K6, Canada.
Dghaym
Rania D
RD
Arndtsen
Bruce A
BA
D000596:Amino Acids / Q000138:chemical synthesis*; D002384:Catalysis; D010080:Oxazoles / Q000737:chemistry*; D010087:Oxides / Q000737:chemistry*; D010165:Palladium / Q000737:chemistry
D000596:Amino Acids; D010080:Oxazoles; D010087:Oxides; D010165:Palladium