Synthesis of 2-methyl- and 2-methylenecyclobutane amino acids
- Avenoza, A. 1
- Busto, J.H. 1
- Peregrina, J.M. 1
- Pérez-Fernández, M. 1
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1
Universidad de La Rioja
info
ISSN: 0040-4020
Año de publicación: 2005
Volumen: 61
Número: 16
Páginas: 4165-4172
Tipo: Artículo
Otras publicaciones en: Tetrahedron
Resumen
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. © 2005 Elsevier Ltd. All rights reserved.