Stereoselective Synthesis of Dienic Nitrogen Compounds

Ramzi Aït Youcef; Charlotte Boucheron; Stéphane Guillarme; Stéphanie Legoupy; Didier Dubreuil; François Huet

doi:10.1055/s-2006-926303

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Synthesis 2006(4): 633-636
DOI: 10.1055/s-2006-926303

PAPER

Stereoselective Synthesis of Dienic Nitrogen Compounds

Ramzi Aït Youcef^a, Charlotte Boucheron^a, Stéphane Guillarme^a, Stéphanie Legoupy*^a, Didier Dubreuil^b, François Huet*^a
^a Laboratoire de Synthèse Organique, UCO2M, UMR CNRS 6011, Université du Maine, avenue Olivier Messiaen, 72085 Le Mans cedex 9, France
^b Laboratoire de Synthèse Organique, UMR CNRS 6513, FR CNRS 2465, 2 rue de la Houssinière, BP 92208, 44322 Nantes cedex 03, France
Fax: +33(2)43833902; e-Mail: stephanie.legoupy@univ-lemans.fr; e-Mail: francois.huet@univ-lemans.fr;

Further Information

Publication History

Received 1 July 2005
Publication Date:
19 January 2006 (online)

Abstract
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Abstract

Eight dienic nitrogen compounds were prepared starting from cyclobutene lactam 8. Dienes 12-15 were obtained by benzylation or acylation followed by methanolysis, hydrolysis or reduction. The unsubstituted lactam 8 provided diene 16. The latter was a precursor for the mono and biacylated products 17-19.

Key words

electrocyclic reactions - lactams - ring opening - dienes - torquoselectivity

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