First asymmetric synthesis of (Un)saturated 1-Alkylbenzo[c]azepin-3-ones: Extension to the corresponding benzazeplnes

Abstract

A flexible route for the stereoselective synthesis of a variety of structurally diverse (1R)-1-alkyldihydro and tetrahydro-benzazepin(ones) has been developed. The key step is a highly diastereoselective 1,2-addition process applied to a stereopure aromatic hydrazone combined with a ring-closing metathesis reaction to secure the formation of the seven-membered azaheterocycle ring system. © 2009 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.