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Truncated diastereoselective Passerini reaction, a rapid construction of polysubstituted oxazole and peptides having an α-hydroxy-β-amino acid component

Guylaine Cuny, Rocio Gámez-Montaño and Jieping Zhu*

*Institut de Chimie des Substances Naturelles, CNRS, 91198, Gif-sur-Yvette Cedex, France, Email:

G. Cuny, R. Gamez-Montano, J. Zhu, Tetrahedron, 2004, 60, 4879-4885.

DOI: 10.1016/j.tet.2004.03.084


The reaction of aldehydes and ketones, including aliphatic and aromatic ones, with amides of α-isocyano-β-phenylpropionic acid in toluene in the presence of lithium bromide gives 2,4,5-trisubstituted oxazoles in good to excellent yield.

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Key Words

Diastereoselectivity, N,N-Dibenzyl aminoaldehyde, α-Hydroxy-β-amino acid, Multicomponent reactions, Oxazoles, Passerini reaction

ID: J72-Y2004-440