Atropisomers of 1-(acyl or aroyl)-2-naphthylindolines. Isolation,X-ray crystal structure and conformational analysis |
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Authors: | Ito Fumikazu Moriguchi Tetsuya Yoshitake Yasuyuki Eto Masashi Yahara Shoji Harano Kazunobu |
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Institution: | Faculty of Pharmaceutical Sciences, Kumamoto University, Kumamoto, Japan. |
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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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