4.8 Article

Atropisomeric Properties of the Dibenzo[b,d]azepin-6-one Nucleus

Journal

ORGANIC LETTERS
Volume 10, Issue 21, Pages 4871-4874

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/ol801968b

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Funding

  1. Japan Society for the Promotion Of Sciences [19590108]
  2. Takeda Pharmaceutical Co. Ltd.
  3. Grants-in-Aid for Scientific Research [19590108] Funding Source: KAKEN

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Dibenzo[b,d]azepin-6-ones (2a,b) were separated by chiral HPLC into the aR- and aS-atropisomers with high stereochemical stability, and methylation at C7 of 2a stereoselectively gave the (aR*,7R*) isomer (4a), which converted to the thermodynamically stable (aS*,7R*) atropisomer (5a) after heating.

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