Simple Preparation of N-Benzyl-β-aminohydroxamic Acids by 1,3-Dipolar Cycloaddition­ of Nitrones

Carine Chevrier; Albert Defoin

doi:10.1055/s-2003-39412

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Synthesis 2003(8): 1221-1224
DOI: 10.1055/s-2003-39412

PAPER

Simple Preparation of N-Benzyl-β-aminohydroxamic Acids by 1,3-Dipolar Cycloaddition of Nitrones

Carine Chevrier, Albert Defoin*
Laboratoire de Chimie Organique et Bioorganique UMR 7015, Ecole Nationale Supérieure de Chimie de Mulhouse, Université de Haute-Alsace., 3, rue Alfred Werner, 68093 Mulhouse Cédex, France
Fax: +33(3)89336875; e-Mail: A.Defoin@uha.fr;

Further Information

Publication History

Received 11 March 2003
Publication Date:
26 May 2003 (online)

Abstract
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Abstract

β-Aminohydroxamic acids 6a-d are prepared in 4 steps and 30-45% overall yield from nitrones 1a-d by 1,3-dipolar cycloaddition with phenyl vinyl ether, N-benzylation, thermal rearrangement, and nucleophilic substitution of the formed phenyl ester with hydroxylamine.

Key words

β-amino acids - hydroxamic acids - cycloaddition - rearrangement

References

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