Synthetic versatility of N-(silylmethyl)imines : Water-induced generation of N-protonated azomethine ylides of nonstabilized type and fluoride-induced generation of 2-azaallyl anions.
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概要
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<I>N</I>-(Silylmethyl)imines generate <I>N</I>-protonated azomethine ylides of nonstabilized type when treated with water in HMPA, which undergo stereospecific and regioselective cycloadditions with electron-poor olefins affording <I>N</I>-unsubstituted pyrrolidines. On the other hand, fluoride-induced desilylation of the imines leads to 2-azaallyl anions which are found to be synthetic equivalents of aminomethyl anion in the Michael additions with electron-poor olefins and nucleophilic additions with carbonyl compounds.
- 公益社団法人 日本化学会の論文
著者
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Matsuda Koyo
Research Institute of Industrial Science, and Department of Molecular Science and Technology, Interdisciplinary Graduate School of Engineering Sciences, Kyushu University
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Tsuge Otohiko
Research Institute of Industrial Science, and Department of Molecular Science and Technology, Interdisciplinary Graduate School of Engineering Sciences Kyushu University
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Kanemasa Shuji
Research Institute of Industrial Science, and Department of Molecular Science and Technology, Interdisciplinary Graduate School of Engineering Sciences Kyushu University
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Hatada Akira
Research Institute of Industrial Science, and Department of Molecular Science and Technology, Interdisciplinary Graduate School of Engineering Sciences, Kyushu University
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Kanemasa Shuji
Research Institute of Industrial Science, and Department of Molecular Science and Technology, Interdisciplinary Graduate School of Engineering Science, Kyushu University
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