Stereoselective Synthesis of Previously Unattainable Enantio(diastereo)enriched Bridged Tetrahydro-2-benzazepines.

Pierre Grandclaudon; Axel Couture,; Stéphane Lebrun; David Dumoulin

doi:10.3390/ecsoc-14-00408

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Stereoselective Synthesis of Previously Unattainable Enantio(diastereo)enriched Bridged Tetrahydro-2-benzazepines.

Pierre Grandclaudon

Axel Couture,

^*,

Stéphane Lebrun

David Dumoulin

¹ Université Lille Nord de France, F-59000 Lille, France
² USTL, Laboratoire de Chimie Organique Physique, EA CMF 4478, Bâtiment C3(2), F-59655Villeneuve d'Ascq, France
³ CNRS, UMR 8181 'UCCS', F-59655 Villeneuve d'Ascq, France

Published: 19 October 2010 by MDPI in The 14th International Electronic Conference on Synthetic Organic Chemistry session General Organic Synthesis

https://doi.org/10.3390/ecsoc-14-00408

Abstract: A new and flexible route for the asymmetric synthesis of a variety of alkylated bridged tetrahydro-2-benzazepines has been developed. The key steps are the highly diastereoselective Michael addition of metalated SAMP-hydrazones to α,β-unsaturated esters combined with cyclomethylenation/Mitsunobu coupling reactions to secure the formation of the seven-membered azaheterocycle and of the bridged unit respectively.

Keywords: SAMP-hydrazones, Michael addition, cyclization, Mitsunobu reaction

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Pierre Grandclaudon

Axel Couture,

Stéphane Lebrun

David Dumoulin