Tetrahedron

Aerobic oxidative dimerization of 1-naphthols to 2, 2′-binaphthoquinones mediated by SnCl 4 and its application to natural product synthesis

T Takeya, H Doi, T Ogata, I Okamoto, E Kotani

文献索引：Takeya, Tetsuya; Doi, Hirohisa; Ogata, Tokutaro; Okamoto, Iwao; Kotani, Eiichi Tetrahedron, 2004 , vol. 60, # 41 p. 9049 - 9060

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被引用次数: 17

摘要

We developed a simple method for the direct synthesis of 2, 2′-binaphthoquinones, utilizing oxidative dimerization via electron donor–acceptor complex formation of 1- naphthols with SnCl4 in the presence of dioxygen. This oxidation involves a catalytic cycle of SnCl4, and the reaction mechanism is discussed. As an application of this method to natural products synthesis, we describe facile biomimetic syntheses of the binaphthoquinones 3, ...