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