Selective Michael-Aldol Reaction by use of Sterically Hindered Aluminum Aryloxides as Lewis Acids: An Easy Approach to Cyclobutane Amino Acids

  1. Avenoza, A. 1
  2. Busto, J.H. 1
  3. Canal, N. 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:
Organic Letters

ISSN: 1523-7060

Año de publicación: 2005

Volumen: 7

Número: 16

Páginas: 3597-3600

Tipo: Artículo

DOI: 10.1021/OL0514707 PMID: 16048351 SCOPUS: 2-s2.0-23944505182 WoS: WOS:000230858500052 GOOGLE SCHOLAR

Otras publicaciones en: Organic Letters

Repositorio institucional: lock_openAcceso abierto Editor

Resumen

(Chemical Equation Presented) A formal [2 + 2] cycloaddition of 2-amidoacrylates with monosubstituted donor olefins, including its asymmetric version, is described. The stereoselectivity of this reaction can be modulated by the use of sterically hindered aluminum aryloxides or methylaluminoxane as Lewis acids. The reaction was applied to the synthesis of both stereoisomers of 2-benzyloxycyclobutane-α-amino acid, which are protected serine analogues c4Ser(OBn). © 2005 American Chemical Society.