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

  1. Avenoza, A. 1
  2. Busto, J.H. 1
  3. Peregrina, J.M. 1
  4. Pérez-Fernández, M. 1
  1. 1 Universidad de La Rioja
    info

    Universidad de La Rioja

    Logroño, España

    ROR https://ror.org/0553yr311

Revista:
Tetrahedron

ISSN: 0040-4020

Año de publicación: 2005

Volumen: 61

Número: 16

Páginas: 4165-4172

Tipo: Artículo

DOI: 10.1016/J.TET.2005.02.039 SCOPUS: 2-s2.0-19344364058 WoS: WOS:000228319200028 GOOGLE SCHOLAR

Otras publicaciones en: Tetrahedron

Repositorio institucional: lock_openAcceso abierto Editor

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.