Formal [2+2] Cycloaddition of 2-Acylaminoacrylates with Vinyl Sulfides. An Approach to Cyclobutane-alfa-Amino Acids as S-Phenylcysteine Analogues

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

    Universidad de La Rioja

    Logroño, España

    ROR https://ror.org/0553yr311

Revista:
Synthesis (Stuttgart)

ISSN: 0039-7881

Año de publicación: 2008

Volumen: 5

Páginas: 743-746

Tipo: Artículo

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DOI: 10.1055/S-2008-1032171 SCOPUS: 2-s2.0-40849094696 WoS: WOS:000254189300012 GOOGLE SCHOLAR

Otras publicaciones en: Synthesis (Stuttgart)

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Resumen

Two new types of conformationally restricted S-phenylcysteine are presented. The restriction comprises a cyclobutane unit that includes the α- and β-carbons of the α-amino acid. The synthetic strategy is based on a formal [2+2] cycloaddition between 2-(acylamino)acrylates as acceptor alkenes and vinyl sulfides as donor alkenes, promoted by aluminum-derived bulky Lewis acids. © Georg Thieme Verlag Stuttgart.