Beilstein J. Org. Chem.2019,15, 852–857, doi:10.3762/bjoc.15.82
synthesis of a novel category of pseudo-peptides via intramolecular Ugi reaction of levulinic acid (4-oxopentanoic acid), aromatic and aliphatic amines, and aminoacid-basedisocyanides is reported. Levulinic acid was applied as a bifunctional substrate containing both carbonyl and acid moieties suitable
for the Ugi reaction. This article provides a facile and convenient one-pot procedure for the synthesis of peptide-like heterocyclic molecules containing 2-pyrrolidone (γ-lactam), amide and ester functional groups with good to excellent yields.
Keywords: aminoacid-basedisocyanides; levulinic acid
acid, aromatic and aliphatic amines and aminoacid-basedisocyanides. First of all, racemic α-amino acids such as DL-tryptophan, DL-phenylalanine and DL-leucine were used as amine source for the synthesis of isocyanide esters 3 through three sequential reactions [30][31]. The first reaction is
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Graphical Abstract
Scheme 1:
Synthesis of amino acid-based isocyanides starting from α-amino acids.