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Synthesis 2007(20): 3201-3204  
DOI: 10.1055/s-2007-990803
PAPER
© Georg Thieme Verlag Stuttgart · New York

Microwave-Assisted Transformation of Esters into Hydroxamic Acids

Assunta Massaroa, Alessandro Mordini*b, Gianna Reginatob, Francesco Russob, Maurizio Taddeic
a ProtEra S.r.l., University Scientific Campus, Viale delle Idee 22, 50019 Sesto Fiorentino, Italy
b ICCOM-CNR, Dipartimento di Chimica Organica ‘U. Schiff’, Via della Lastruccia 13, 50019 Sesto Fiorentino, Italy
Fax: +39(055)4573580; e-Mail: alessandro.mordini@unifi.it;
c Dipartimento Farmaco Chimico Tecnologico, Università degli Studi di Siena, Via A. Moro 2, 53100 Siena, Italy
Further Information

Publication History

Received 26 June 2007
Publication Date:
21 September 2007 (online)

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Abstract

A general, mild and efficient procedure with which to access hydroxamic acids, in good yields and purity, is reported. Esters are used as substrates and reacted with hydroxylamine, in the presence of a base, under microwave activation. The method has been successfully applied to enantiomerically pure esters without loss of stereochemical integrity.

Key words

esters - chemoselectivity - hydroxamic acid - microwave reactions - metalloproteinases

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