Atropisomers of 1-(acyl or aroyl)-2-naphthylindolines. Isolation, X-ray crystal structure and conformational analysis
Fumikazu Ito1, Tetsuya Moriguchi, Yasuyuki Yoshitake
1Faculty of Pharmaceutical Sciences, Kumamoto University, Kumamoto, Japan.
Abstract:
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.
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