SYNTHESIS OF ALPHA,OMEGA-DIAMINO ACIDS VIA AMIDOCARBONYLATION REACTION - NOVEL SYNTHESIS OF LYSINE, ORNITHINE, AND THEIR ANALOGS

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