A Zr-catalyzed synthesis of tetrasubstituted 1,3-diacylpyrroles
is reported that employs the direct use ofN-acyl
α-aminoaldehydes with 1,3-dicarbonyl compounds. The products
were formed in up to 88% yield and shown to be hydrolytically and
configurationally stable under the reaction conditions (THF/1,4-dioxane
and H2O). TheN-acyl α-aminoaldehydes
were readily prepared from the corresponding α-amino acids.
The reaction tolerates a wide array of substrate types including alkyl-,
aryl-, heteroaryl-, and heteroatom-containing groups on the aminoaldehyde
side chain. A variety of 1,3-dicarbonyls proved amenable to the reaction
along with an aldehyde derived from al,l-dipeptide,
an aldehyde generatedin situ, and anN-acylated glucosamine.