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Paper | Regular issue | Vol 68, No. 1, 2006, pp.101-110
Published online, 1st November, 2005
DOI: 10.3987/COM-05-10579
Synthesis of Naphthothiazolium Salts from BINOL

Osamu Hara, Taiju Nakamura, Kazuishi Makino, and Yasumasa Hamada*

*Faculty of Pharmaceutical Sciences, Chiba University, 1-33 Yayoi-cho, Inage-ku, Chiba 263-8522, Japan


Naphthothiazolium salts with axial chirality were prepared from (S)-BINOL through introduction of a thiol group in place of the hydroxyl group by the Newmann-Kwart rearrangement and construction of the thiazolium ring by treatment of the air-sensitive N-alkylated aminothionaphthol with triethyl orthoformate in the presence of hydrogen chloride.