Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 81, Issue 8, Pages 3136-3148Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.5b02900
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Funding
- Japan Society for the Promotion of Sciences [25460154, 25860091]
- Grants-in-Aid for Scientific Research [25460154, 15K08032, 15H00923, 25860091] Funding Source: KAKEN
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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.
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