Coupling reaction of 2-hydroxyindoline with arenes by BF3·Et2O. A convenient synthetic method of isolable diasteromeric atropisomers
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.
Kitamura,Harano,Hisano
p. 2255 - 2261
(2007/10/02)
A CONVENIENT SYNTHETIC METHOD OF 1-ACYL-2-ARYL-3,3-DIMETHYLINDOLINE INVOLVING ISOLABLE DIASTEREOMERIC ATROPISOMERS
The synthesis of 1-acyl-2-aryl-3,3-dimethylindoline was improved by the reaction of 1-acyl-2-hydroxy-3,3-dimethylindoline with an arene in the presence of BF3*O(C2H5)2 in dioxane, and stable diastereomeric atropisomers were isolated as products when the a