Events The 14th International Electronic Conference on Synthetic Organic Chemistry

Event submissions

Published

This submission belongs to the session a. General Organic Synthesis of the event The 14th International Electronic Conference on Synthetic Organic Chemistry

Published date

19 Oct, 2010

Citation

Pierre Grandclaudon, Axel Couture,, Stéphane Lebrun, David Dumoulin, Stereoselective Synthesis of Previously Unattainable Enantio(diastereo)enriched Bridged Tetrahydro-2-benzazepines., in Proceedings of The 14th International Electronic Conference on Synthetic Organic Chemistry, 1 November–30 November 2010, MDPI: Basel, Switzerland, doi: 10.3390/ecsoc-14-00408

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

Pierre Grandclaudon ^1,2,3

Axel Couture, ^1,2,3

Stéphane Lebrun ^1,2,3

David Dumoulin ^1,2,3

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

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

Molecular Modeling:Prediction of the structure of Host-Guest complexes

Unexpected S(O) 2 –O Bond Scission upon Anionic Cycliarylation of Cyclic Sulfamidates. A New Route to N-Functionalized Benzosultams.