Zr-Catalyzed Synthesis of Tetrasubstituted 1,3-Diacylpyrroles from N-Acyl -Aminoaldehydes and 1,3-Dicarbonyls

A Zr-catalyzed synthesis of tetrasubstituted 1,3-diacylpyrrolesis reported that employs the direct use of N-acyl alpha-aminoaldehydes with 1,3-dicarbonyl compounds. The productswere formed in up to 88% yield and shown to be hydrolytically andconfigurationally stable under the reaction conditions (THF/1,4-dioxaneand H2O). The N-acyl alpha-aminoaldehydeswere readily prepared from the corresponding alpha-amino acids.The reaction tolerates a wide array of substrate types including alkyl-,aryl-, heteroaryl-, and heteroatom-containing groups on the aminoaldehydeside chain. A variety of 1,3-dicarbonyls proved amenable to the reactionalong with an aldehyde derived from a l,l-dipeptide,an aldehyde generated in situ, and an N-acylated glucosamine.