21819-50-1Relevant academic research and scientific papers
Role of 2-naphthyl ether intermediate in formation of isolable atropisomers derived from the coupling reaction of (2-hydroxy-3,3-dimethylindolin-l-yl)-(substituted phenyl)methanones with 2-naphthol
Eto, Masashi,Ito, Fumikazu,Sato, Hidetoshi,Shinohara, Itaru,Yamaguchi, Koki,Yoshitake, Yasuyuki,Harano, Kazunobu
experimental part, p. 1485 - 1496 (2009/12/24)
The formation pathway of the atropisomers derived from the reaction of (2-hydroxy-3,3-dimethylindolin-l-yl)(4-substituted phenyl)methanones with 2-naphthol in the presence of BF3·Et2O was discussed on the basis of the isolation of the 2-naphthyl ether intermediate whose structure was determined by single crystal X-ray analysis. The results indicate that the coupling reaction proceeds through stepwise mechanism, i.e., the ether intermediate formation followed by Fries-type rearrangement.
Coupling reaction of 2-hydroxyindoline with arenes by BF3·Et2O. A convenient synthetic method of isolable diasteromeric atropisomers
Kitamura,Harano,Hisano
, p. 2255 - 2261 (2007/10/02)
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.
Crystallographic Analysis of a Pair of Isolable Atropisomers of 2-Aryl Substituted Indoline Derivatives
Eto, Masashi,Harano, Kazunobu,Hisano, Takuzo,Kitamura, Takeo
, p. 311 - 315 (2007/10/02)
The cystal and molecular structures of isomeric compounds of 1-(4'-chlorobenzoyl)-2-(2''-hydroxynaphthyl)-3,3-dimethylindoline have been determined by single crystal X-ray analyses as a pair of diastereomeric atropisomers due to restricted rotation about
A CONVENIENT SYNTHETIC METHOD OF 1-ACYL-2-ARYL-3,3-DIMETHYLINDOLINE INVOLVING ISOLABLE DIASTEREOMERIC ATROPISOMERS
Kitamura, Takeo,Koga, Toshitaka,Taguchi, Tanezo,Harano, Kazunobu
, p. 1315 - 1318 (2007/10/02)
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
