Atropisomeric properties of 7-, 8-, and 9-membered-ring dibenzolactams: Conformation, thermal stability, and chemical reactivity

Journal of Organic Chemistry

Volumn 75, Issue 17, 2010, Pages 5984-5993

  Tabata, Hidetsugu ^a   Suzuki, Hiroyuki ^a   Akiba, Kumi ^a   Takahashi, Hideyo ^a   Natsugari, Hideaki ^a  

^a TEIKYO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

8-MEMBERED RING; ATROPISOMERS; CHIRAL HPLC; METHYL GROUP; STABLE ISOMERS; STEREO-SELECTIVE; THERMAL STABILITY; THERMODYNAMICALLY STABLE; X-RAY CRYSTALLOGRAPHIC ANALYSIS;

ALKYLATION; CHEMICAL STABILITY; ISOMERS; METHYLATION; STEREOCHEMISTRY;

GROUP TECHNOLOGY;

LACTAM DERIVATIVE; METHYL GROUP;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL REACTION; CHEMICAL STRUCTURE; ENANTIOMER; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; ISOMER; METHYLATION; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY; THERMODYNAMICS; THERMOSTABILITY; X RAY CRYSTALLOGRAPHY;

CHROMATOGRAPHY, HIGH PRESSURE LIQUID; CRYSTALLOGRAPHY, X-RAY; LACTAMS; MODELS, MOLECULAR; MOLECULAR CONFORMATION; STEREOISOMERISM; TEMPERATURE; THERMODYNAMICS;

EID: 77956150680     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo1013383     Document Type: Article

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19. Atropisomeric properties of the 7-membered-ring benzolactams without biphenyl moiety will be reported in due course.
20. 2 R).
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24. The G value was determined based on the time-dependent conversion rate (% ee) estimated from chiral HPLC analysis of a solution of the enantiomers after being allowed to stand at designated temperatures; see: Petit, M.; Lapierre, A. J. B.; Curran, D. P. J. Am. Chem. Soc. 2005, 127, 14994-14995
25. In our previous work, (4) C7-alkylation and isomerization of the alkylated product were examined by using the racemate of 1 (a, b), and the same stereochemical results as described in this paper (Table 2 /entries 1 and 2) were observed in the racemic form.