Tetrahedron: Asymmetry

Synthesis and axial chirality of an enantiopure aminodibenzazepinone

…, D Mitchell, MA Carr, JR Stout, MD Belvo

Index: Cole, Kevin P.; Mitchell, David; Austin Carr; Stout, James R.; Belvo, Matthew D. Tetrahedron Asymmetry, 2009 , vol. 20, # 11 p. 1262 - 1266

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Citation Number: 5

Abstract

A route for the synthesis of (S, S)-7-amino-5-methyl-5H-dibenzo [b, d] azepin-6 (7H)-one hydrochloride is disclosed. The synthesis includes a Friedel–Crafts alkylation to form the seven-membered ring and a highly efficient classical resolution. Additional studies on the enantiopure material showed the amine to be highly resistant to racemization, which led us to investigate the unexpected stability. We propose that the inherent axial chirality ...