Synthesis of .ALPHA.,.OMEGA.-diamino acids via amidocarbonylation reaction: Novel synthesis of lysine, ornithine, and their analogs.

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概要

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• α,ω-Diamino acid derivatives, such as lysine and ornithine, were synthesized via amidocarbonylation (cobalt-catalyzed formation of <I>N</I>-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 <I>N</I>-phthaloyl-β,γ- and <I>N</I>-phthaloyl-γ,δ-unsaturated amines proceeds very nicely to give α,ω-diamino acid derivatives with good selectivity. Selective deprotection of α-<I>N</I>-acyl-ω-<I>N</I>-phthaloyl α,ω-diamino acids was achieved using hydrazine for the <I>N</I>-phthaloyl group and aminoacylase for the <I>N</I>-acetyl group to afford the optically active α,ω-diamino acid, respectively.

• 公益社団法人 日本化学会の論文

著者

• Izawa Kunisuke

  Central Research Laboratories Ajinomoto Co. Inc.

• Amino Yusuke

  Central Research Laboratories, Ajinomoto Co.

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• Synthesis of .ALPHA.,.OMEGA.-diamino acids via amidocarbonylation reaction: Novel synthesis of lysine, ornithine, and their analogs.
• Synthesis of .ALPHA.-amino acids containing a cyclopropane ring via cobalt-catalyzed carbonylation-amidocarbonylation of cyclopropanemethanols.

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