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

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

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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Bibliographische Detailangaben
Veröffentlicht in:Organic letters 2008-11, Vol.10 (21), p.4871-4874
Hauptverfasser: Tabata, Hidetsugu, Akiba, Kumi, Lee, Shoukou, Takahashi, Hideyo, Natsugari, Hideaki
Format: Artikel
Sprache:eng
Schlagworte:
Azepines - chemical synthesis
Azepines - chemistry
Benzene - chemistry
Crystallography, X-Ray
Magnetic Resonance Spectroscopy
Methylation
Models, Molecular
Molecular Structure
Stereoisomerism
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Zusammenfassung: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.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol801968b