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

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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.

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Dumoulin, D., Lebrun, S., Deniau, E., Couture, A., & Grandclaudon, P. (2009). First asymmetric synthesis of (Un)saturated 1-Alkylbenzo[c]azepin-3-ones: Extension to the corresponding benzazeplnes. European Journal of Organic Chemistry, (22), 3741–3752. https://doi.org/10.1002/ejoc.200900365

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