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

Revue:
Organic Letters

ISSN: 1523-7060

Année de publication: 2005

Volumen: 7

Número: 16

Pages: 3597-3600

Type: Article

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

D'autres publications dans: Organic Letters

Dépôt institutionnel: lock_openAccès ouvert Editor

Résumé

(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.