Journal
TETRAHEDRON
Volume 60, Issue 22, Pages 4879-4885Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2004.03.084
Keywords
diastereoselectivity; N,N-dibenzyl aminoaldehyde; (alpha-hydroxy-beta-amino acid; multicomponent reaction; oxazole; Passerini reaction
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The reaction of aldehydes and ketones, including aliphatic and aromatic ones, with amides of alpha-isocyano-beta-phenylpropionic acid in toluene in the presence of lithium bromide gives 2,4,5-trisubstituted oxazoles in good to excellent yield. Protected chiral alpha-amino aldehydes participate in this reaction to give, after hydrolysis of the oxazoles, norstatine-containing peptides in good overall yield. The nucleophilic addition of isonitriles to N,N-dibenzyl phenylalanal is investigated for the first time and is found to be stereoselective leading predominantly to the anti-adduct (dr=9/1). On the other hand, the reaction between the N-Boc phenylalanal and isonitrile is non-stereoselective. (C) 2004 Elsevier Ltd. All rights reserved.
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