Synthesis of α,ω-Diamino Acids via Amidocarbonylation Reaction: Novel Synthesis of Lysine, Ornithine, and Their Analogs

Abstract

Abstract α,ω-Diamino acid derivatives, such as lysine and ornithine, were synthesized via amidocarbonylation (cobalt-catalyzed formation of N-acyl α-amino acid from aldehyde, amide and carbon monoxide) of ω-(phthalimido)alkanals in good yield. The phthalimido group was proved to be intact under the conditions of amidocarbonylation. The hydroformylation-amidocarbonylation of N-phthaloyl-β,γ- and N-phthaloyl-γ,δ-unsaturated amines proceeds very nicely to give α,ω-diamino acid derivatives with good selectivity. Selective deprotection of α-N-acyl-ω-N-phthaloyl α,ω-diamino acids was achieved using hydrazine for the N-phthaloyl group and aminoacylase for the N-acetyl group to afford the optically active α,ω-diamino acid, respectively.