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Synthesis 2011(17): 2781-2788  
DOI: 10.1055/s-0030-1260132
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

N-Bromosuccinimide-Promoted Cyclization of β-Carboxymethyl Enamino Esters; Synthesis of Functionalized 4-Amino-2(5H)-Furanones

Valérie Toum, Catherine Kadouri-Puchot*, Louis Hamon, Gérard Lhommet, Virginie Mouriès-Mansuy, Corinne Vanucci-Bacqué, Luc Dechoux*
Université Pierre et Marie Curie-Paris 6, Institut Parisien de Chimie Moléculaire, UMR 7201, 4 place Jussieu, case courrier 47, 75005 Paris, France
Fax: +33(1)44275097; e-Mail: luc.dechoux@upmc.fr;
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Publication History

Received 6 April 2011
Publication Date:
21 July 2011 (online)

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Abstract

An easy, two-step approach to various 5-carboxymethyl-2(5H)-furanones is described. A detailed study of the reaction of β-carboxymethyl enamino esters with N-bromosuccinimide is presented.

Key words

tetronamides - 4-amino-2(5H)-furanones - bromocyclization - alkylation - decarborxylation

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Data were obtained from reactions with less than 5% deviation