Chemical and Pharmaceutical Bulletin p. 2255 - 2261 (1992)
Update date:2022-08-04
Topics:
Kitamura
Harano
Hisano
A simple method for synthesis of 2-aryl-substituted 3,3-dimethylindoline derivatives was established by the reaction of 1-acyl-2-hydroxy-3,3-dimethylindoline with electron-rich arenes in the presence of boron trifluoride-diethylether in dioxane. In the reaction with β-naphthol, a pair of isolable diastereomeric atropisomers was isolated. The conformations of both atropisomers were determined by single crystal X-ray analyses. The substitution reaction behavior toward various arenes was accounted for in terms of frontier molecular orbital (FMO) theory.
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