title: Stereochemistry of N-Benzoyl-5-substituted-1-benzazepines Revisited: Synthesis of the Conformationally Biased Derivatives and Revision of the Reported Structure.
abstract: The syn (aR*,5R*) and anti (aS*,5R*) diastereomers of N-benzoyl-C5-substituted-1-benzazepines originating in the chiralities at C5 and the Ar-N(C═O) axis were first stereoselectively synthesized by biasing the conformation with a substituent at C6 and C9, respectively. Detailed examination of the stereochemistry (i.e., conformation and configuration) of these N-benzoyl-1-benzazepines by X-ray crystallographic analysis, VT NMR, and DFT calculations revealed new physicochemical aspects of these heterocycles including revision of the stereochemistry previously reported.
authors.affiliation: Faculty of Pharma Sciences, Teikyo University , 2-11-1 Kaga, Itabashi-ku, Tokyo 173-8605, Japan.
authors.forename: Hidetsugu
authors.initials: H
authors.lastname: Tabata
authors.affiliation: Faculty of Pharma Sciences, Teikyo University , 2-11-1 Kaga, Itabashi-ku, Tokyo 173-8605, Japan.
authors.forename: Tetsuya
authors.initials: T
authors.lastname: Yoneda
authors.affiliation: Affinity Science Corporation , 1-11-1 Nishigotanda, Shinagawa-ku, Tokyo 141-0031, Japan.
authors.forename: Tomohiko
authors.initials: T
authors.lastname: Tasaka
authors.affiliation: Department of Applied Chemistry, Graduate School of Science and Engineering, Tokyo Institute of Technology , Meguro-ku, Tokyo 152-8552, Japan.
authors.forename: Shigekazu
authors.initials: S
authors.lastname: Ito
authors.affiliation: Faculty of Pharma Sciences, Teikyo University , 2-11-1 Kaga, Itabashi-ku, Tokyo 173-8605, Japan.
authors.forename: Tetsuta
authors.initials: T
authors.lastname: Oshitari
authors.affiliation: Faculty of Pharma Sciences, Teikyo University , 2-11-1 Kaga, Itabashi-ku, Tokyo 173-8605, Japan.
authors.forename: Hideyo
authors.initials: H
authors.lastname: Takahashi
authors.affiliation: Faculty of Pharma Sciences, Teikyo University , 2-11-1 Kaga, Itabashi-ku, Tokyo 173-8605, Japan.
authors.forename: Hideaki
authors.initials: H
authors.lastname: Natsugari