4.7 Article

Isolation and Characterization of Atropisomers of Seven-Membered-Ring Benzolactams

Journal

JOURNAL OF ORGANIC CHEMISTRY
Volume 76, Issue 12, Pages 5123-5131

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/jo2008725

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Funding

  1. Japan Society for the Promotion of Sciences [21590124, 21790025]
  2. Grants-in-Aid for Scientific Research [21790025, 21590124] Funding Source: KAKEN

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The atropisomeric properties of seven-membered-ring benzolactams (7a-c and 8a) [1,5-benzodiazepin-2-one (a), 1,5-benzothiazepin-4-one (b), and 1-benzazepin-2-one (c)] were examined. The atropisomers were isolated as the diastereomers with an (S)-phenethylamide moiety, which were characterized by X-ray crystallography, and the barriers to their interconversion were clarified.

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