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
-
1
Universidad de La Rioja
info
ISSN: 1523-7060
Year of publication: 2005
Volume: 7
Issue: 16
Pages: 3597-3600
Type: Article
More publications in: Organic Letters
Abstract
(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.