Synthesis of (diethoxyphosphoryl)acetonitrile oxide and its cycloaddition to olefins. Synthetic applications to 3,5-disubstituted 2-isoxazolines.
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概要
- 論文の詳細を見る
(Diethoxyphosphoryl)acetonitrile oxide undergoes regioselective cycloaddition to olefins leading to 3-[(diethoxyphosphoryl)methyl]-2-isoxazolines or -isoxazole. The phosphorus-stabilized carbanions generated by deprotonation of the cycloadducts can be utilized for the condensation with carbonyl compounds, alkylation, and oxidation with oxygen to provide 3,5-disubstituted 2-isoxazolines as useful synthetic building blocks. Raney nickel hydrogenolysis of 3-[(diethoxyphosphoryl)methyl]-2-isoxazolines gives β-hydroxy-β′-phosphoryl ketones bearing a variety of functional groups, which can be further converted into α,β-unsaturated β′-phosphoryl ketones.
- 公益社団法人 日本化学会の論文
著者
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SUGA Hiroyuki
Institute for Medical and Dental Engineering, Tokyo Medical and Dental University
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Kanemasa Shuji
Institute Of Advanced Material Study Kyushu University
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Tsuge Otohiko
Institute of Advanced Material Study, and Department of Molecular Science and Technology, Interdisciplinary Graduate School of Engineering Sciences
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Nakagawa Norihiko
Institute of Advanced Material Study, and Department of Molecular Science and Technology, Interdisciplinary Graduate School of Engineering Sciences, Kyushu University
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