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Asymmetric Synthesis of 1- ,3- or 4-Alkyl- or Aryl- Tetrahydro-Benzo[c]azepines
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1  UMR CNRS 8009 "Chimie Organique et Macromoléculaire", Université des Sciences et Technologies de Lille 1, Laboratoire de Chimie Organique Physique, Bâtiment C3(2), F-59655 Villeneuve d'Ascq Cedex, France

Abstract: Flexible routes for the stereoselective synthesis of a variety of structurally diverse 1-, 3- or 4-alkyl and aryl-tetrahydrobenzo[c]azepines have been developed. The key steps are the highly diastereoselective 1,2-addition process or metallation/alkylation sequence applied to stereopure hydrazones. Subsequent cyclomethylenation or ringclosing metathesis reaction to secure the formation of the seven-membered azaheterocycle ring system complete the assembly of the targeted titled compounds.