First Asymmetric Synthesis of (Un)saturated 1-Alkylbenzo[c]azepin-3-ones: Extension to the Corresponding Benzazepines

✍ Scribed by David Dumoulin; Stéphane Lebrun; Eric Deniau; Axel Couture; Pierre Grandclaudon

• Publisher: John Wiley and Sons
• Year: 2009
• Tongue: English
• Weight: 294 KB
• Volume: 2009
• Category: Article
• ISSN: 1434-193X
• DOI: 10.1002/ejoc.200900365

✦ Synopsis

Abstract

A flexible route for the stereoselective synthesis of a variety of structurally diverse (1R)‐1‐alkyldihydro and tetrahydrobenzazepin(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.(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)