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1,2-ジオール分子認識に基づく選択的分子変換反応
http://hdl.handle.net/10069/16318
http://hdl.handle.net/10069/16318f9580667-0168-45cb-be32-765f0bc4c6dc
名前 / ファイル | ライセンス | アクション |
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JSOCJ_65_216.pdf (956.6 kB)
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Item type | 学術雑誌論文 / Journal Article(1) | |||||
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公開日 | 2008-04-07 | |||||
タイトル | ||||||
タイトル | 1,2-ジオール分子認識に基づく選択的分子変換反応 | |||||
言語 | ||||||
言語 | jpn | |||||
キーワード | ||||||
主題Scheme | Other | |||||
主題 | molecular recognition | |||||
キーワード | ||||||
主題Scheme | Other | |||||
主題 | 1,2-diols | |||||
キーワード | ||||||
主題Scheme | Other | |||||
主題 | kinetic resolution | |||||
キーワード | ||||||
主題Scheme | Other | |||||
主題 | asymmetric desymmetrization | |||||
キーワード | ||||||
主題Scheme | Other | |||||
主題 | benzoylation | |||||
キーワード | ||||||
主題Scheme | Other | |||||
主題 | oxidation | |||||
キーワード | ||||||
主題Scheme | Other | |||||
主題 | electrochemical oxidation | |||||
資源タイプ | ||||||
資源タイプ識別子 | http://purl.org/coar/resource_type/c_6501 | |||||
資源タイプ | journal article | |||||
著者 |
松村, 功啓
× 松村, 功啓× 尾野村, 治× 出水, 庸介 |
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著者別名 | ||||||
姓名 | Matsumura, Yoshihiro | |||||
著者別名 | ||||||
姓名 | Onomura, Osamu | |||||
著者別名 | ||||||
姓名 | Demizu, Yosuke | |||||
その他のタイトル | ||||||
その他のタイトル | Selective molecular transformation of 1,2-diols based on molecular recognition | |||||
抄録 | ||||||
内容記述タイプ | Abstract | |||||
内容記述 | On the bases of the concept that a coordination of 1,2-diols 1 with an appropriate metal ion(M^n+) might form an activated five-membered intermediate in which the OH group is much activated than those of non-activated 1, we examined a monobenzoylation of 1 by benzoyl chloride using tin and copper ions as M^n+. As the results, the monobenzoylation of 1 was achieved with high selectivity even in the presence of monools. The monobenzoylation reactions were then applied to kinetic resolution of dl-1 and asymmetric desymmetrization of meso-1 using a chiral organotin or BOX(bisoxazoline)-CuCl_2 as a catalyst. In particular, the asymmetric outcome using (R, R)-Ph-BOX-CuCl_2 catalyst was promising and attractive. That is, the kinetic resolution of dl-1(with up to >99.9% ee for monobenzoylation of hydrobenzoin), its application to a synthesis of D-inositol-1-phosphate (100% ee), the asymmetric desymmetrization of meso-1(with up to 94% ee for monobenzoylation of meso-1,2-hydrobenzoin and 93% ee for monocarbamoylation of meso-l,2-cyclooctanediol), and the asymmetric desymmetrization of meso-1,3-diols(with up to 55% ee for the monobenzoylation of ethyl 2-ethyl-2-hydroxymethyl-3-hydroxypropanoate) were achieved. Also, the method was applied to electrochemical oxidation of 1 and its asymmetric version(38% ee for the asymmetric desymmetrization of meso-hydrobenzoin and 72% ee for the kinetic resolution of dl-hydrobenzoin). | |||||
書誌情報 |
有機合成化学協会誌 en : Journal of synthetic organic chemistry, Japan 巻 65, 号 3, p. 216-225, 発行日 2007-03 |
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出版者 | ||||||
出版者 | 有機合成化学協会 | |||||
ISSN | ||||||
収録物識別子タイプ | ISSN | |||||
収録物識別子 | 00379980 | |||||
書誌レコードID | ||||||
収録物識別子タイプ | NCID | |||||
収録物識別子 | AN0024521X | |||||
著者版フラグ | ||||||
出版タイプ | VoR | |||||
出版タイプResource | http://purl.org/coar/version/c_970fb48d4fbd8a85 | |||||
引用 | ||||||
内容記述タイプ | Other | |||||
内容記述 | 有機合成化学協会誌 65(3) pp.216-225, 2007 |