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Paper | Regular issue | Vol 78, No. 6, 2009, pp.1485-1496
Published online, 9th March, 2009
DOI: 10.3987/COM-09-11644
Role of 2-Naphthyl Ether Intermediate in Formation of Isolable Atropisomers Derived from the Coupling Reaction of (2-Hydroxy-3,3-dimethylindolin-1-yl)(substituted Phenyl)methanones with 2-Naphthol

Masashi Eto, Fumikazu Ito, Hidetoshi Sato, Itaru Shinohara, Koki Yamaguchi, Yasuyuki Yoshitake, and Kazunobu Harano*

*Laboratory of Molecular Design, Sojo University, 4-22-1, Ikeda, Kumamoto-shi, 860-0082, Japan

Abstract

The formation pathway of the atropisomers derived from the reaction of (2-hydroxy-3,3-dimethylindolin-1-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.