Synthesis of 2-methyl- and 2-methylenecyclobutane amino acids

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• 作者：Avenoza ; Alberto ; Busto ; Jesú ; s H. ; Peregrina ; Jesú ; s M. ; Pé ; rez-Ferná ; ndez ; Marta
• 关键词：Amino acid ; Cyclobutane ; Hydrogenation ; Valine
• 刊名：Tetrahedron
• 出版年：2005
• 出版时间：April 18, 2005
• 年：2005
• 卷：61
• 期：16
• 页码：4165-4172
• 全文大小：378 K

文摘

An efficient and easy formal [2+2] cycloaddition (Michael–Dieckmann-type reaction) on methyl 2-acetamidoacrylate with ketene diethyl acetal gave the cyclobutane core. Two kinds of 2-substituted cyclobutane amino acids have been obtained from this compound by means of stereocontrolled interconversion of functional groups: 1-amino-2-methylcyclobutane-1-carboxylic acids (2,4-methanovalines) and 1-amino-2-methylenecyclobutane-1-carboxylic acid. The latter amino acid can be regarded as a restricted α-methyl-α-vinylglycine.