Asymmetric Synthesis of α, α-Disubstituted α-Amino Acids via an Intramolecular Strecker Synthesis

スポンサーリンク

概要

• 論文の詳細を見る

• A series of optically active α, α-disubstituted α-amino acids have been synthesized starting with an achiral or a racemic 2-hydroxy ketone. The key transformation to the present synthesis is an intramolecular version of Strecker synthesis. An α-keto ester having a chiral amino acid as the ester group afforded cyclic amino nitrile, in a highly stereoselective manner, in which the amino group and the chirality were diastereoselectively transplanted into the internal ketone group via an imine-enamine equilibrium of the cyclic ketimine intermediate. Oxidation of the amino group followed by removal of the resulting imino group and hydrolysis of the nitrile group afforded α-hydroxymethyl α-amino acid. The use of L-amino acid as the chirality transferring group gave R enantiomer, and its S enantiomer was obtained when D-amino acid was employed. The syntheses of optically active α-substituted serines, α-methylthreonines, and 1-amino-2-hydroxycycloalkanecarboxylic acids are described.

• 社団法人 有機合成化学協会の論文
• 1997-11-01

著者

• HORIKAWA Manabu

  Suntory Institute for Bioorganic Research

• Ohfune Yasufumi

  Department Of Material Science Faculty Of Science Osaka City University

関連論文

• Suppression of Pseudomonas aeruginosa quorum-sensing systems by macrolides : a promising strategy or an oriental mystery?
• P-534 Studies on the Regulation of the Host Immune System by Pseudomonas Quorum-Sensing Autoinducer, 3-Oxo-Dodecanoylhomoserine Lactone
• Roles of Pseudomonas aeruginosa Autoinducers and their Degradation Products, Tetramic acids, in Bacterial Survival and Behavior in Ecological Niches
• Asymmetric Strecker Route toward the Synthesis of Biologically Active α, α-Disubstituted α-Amino Acids
• Asymmetric Synthesis of α, α-Disubstituted α-Amino Acids via an Intramolecular Strecker Synthesis
• Roles of Pseudomonas aeruginosa Autoinducers and their Degradation Products, Tetramic acids, in Bacterial Survival and Behavior in Ecological Niches

スポンサーリンク