Selective Michael-Aldol Reaction by use of Sterically Hindered Aluminum Aryloxides as Lewis Acids: An Easy Approach to Cyclobutane Amino Acids
- Avenoza, A. 1
- Busto, J.H. 1
- Canal, N. 1
- Peregrina, J.M. 1
- Pérez-Fernández, M. 1
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1
Universidad de La Rioja
info
ISSN: 1523-7060
Ano de publicación: 2005
Volume: 7
Número: 16
Páxinas: 3597-3600
Tipo: Artigo
Outras publicacións en: Organic Letters
Resumo
(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.