Atropisomers of 1-(acyl or aroyl)-2-naphthylindolines. Isolation, X-ray crystal structure and conformational analysis.
A series of pairs of stable diastereomeric atropisomers caused by restricted rotation around the Csp3-Csp2 bond of [2-(2-hydroxynaphthalen-1-yl)-3,3-dimethyl-2,3-dihydroindol-1-yl]-(3- or 4-substituted phenyl)-methanone or [2-(2-hydroxynaphthalen-1-yl)-3,3-dimethyl-2,3-dihydroindol-1-yl]-1-alkanone were isolated. The conformational analyses of the atropisomers were performed based on the X-ray crystallographic and (1)H-NMR spectral data. It became clear that rotation about the C2-naphthyl bond is restricted at room temperature, whereas the >NCO-Ar bond rotates freely.
Ito
Fumikazu
F
Faculty of Pharmaceutical Sciences, Kumamoto University, Kumamoto, Japan.
Moriguchi
Tetsuya
T
Yoshitake
Yasuyuki
Y
Eto
Masashi
M
Yahara
Shoji
S
Harano
Kazunobu
K
D002236:Carbohydrate Conformation; D018360:Crystallography, X-Ray; D007211:Indoles / Q000737:chemistry*; D008958:Models, Molecular; D015394:Molecular Structure; D009281:Naphthalenes / Q000737:chemistry*; D013237:Stereoisomerism
D007211:Indoles; D009281:Naphthalenes