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The Mechanism of the Enantioselective Photocyclization of 2-Piperidone in the Clathrate Crystal
http://hdl.handle.net/10112/5607
http://hdl.handle.net/10112/560779928efc-c027-48b8-84fc-9dd5a4a19cbf
| 名前 / ファイル | ライセンス | アクション |
|---|---|---|
KU-1100-19940900-26.pdf (641.6 kB)
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| Item type | 学術雑誌論文 / Journal Article(1) | |||||
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| 公開日 | 2011-11-21 | |||||
| タイトル | ||||||
| タイトル | The Mechanism of the Enantioselective Photocyclization of 2-Piperidone in the Clathrate Crystal | |||||
| 言語 | ||||||
| 言語 | eng | |||||
| 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 |
Hashizume, Daisuke
× Hashizume, Daisuke× Ohashi, Yuji× Tanaka, Koichi× Toda, Fumio |
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| 著者別名 | ||||||
| 識別子Scheme | WEKO | |||||
| 識別子 | 26402 | |||||
| 姓名 | 橋爪, 大輔 | |||||
| 著者別名 | ||||||
| 識別子Scheme | WEKO | |||||
| 識別子 | 26403 | |||||
| 姓名 | 大橋, 裕二 | |||||
| 著者別名 | ||||||
| 識別子Scheme | WEKO | |||||
| 識別子 | 26404 | |||||
| 姓名 | 田中, 耕一 | |||||
| 著者別名 | ||||||
| 識別子Scheme | WEKO | |||||
| 識別子 | 26405 | |||||
| 姓名 | 戸田, 芙三夫 | |||||
| 概要 | ||||||
| 内容記述タイプ | Other | |||||
| 内容記述 | The achiral molecules of N-(arylcarbonylmethyl)-2-piperidones form 1 : 1 host–guest complexes with the chiral host molecule derived from tartaric acid. The guest molecules in the clathrate crystals are converted into the chiral 7-aryl-7-hydroxy-1-azabicyclo[4.2.0]octan-2-one derivatives with high optical yields on exposure to a high pressure Hg lamp. The crystal structures and absolute configurations of the clathrate compound (5a), which consists of (−)-(2R,3R)-2,3-bis(hydroxydiphenylmethyl)-1,4-dioxaspiro[4.5]decane (4) and N-(p-bromophenylcarbonylmethyl)-2-piperidone (1a), and of the chiral product of (−)-(6S,7S)-7-hydroxy-1-azabicyclo[4.2.0]octan-2-one (2a) were determined by X-rays. (5a) C34H34O4·C13H14NO2Br, fw = 802.81, monoclinic C2, a = 24.186(3), b = 9.550(3), c = 19.711(3) Å, β=116.18(1)°,V = 4086(2) Å3, Z = 4, final R became 0.047. (2a) C13H14NO2Br, fw = 296.16, orthorhombic, P212121, a = 7.047(2), b = 31.151(3), c = 5.696(2) Å, V = 1250.3(5) Å3, Z = 4, final R became 0.039. The enantioselectivity of the photocyclization is clearly explained by the two structures if we assume that the reaction proceeds topochemically. | |||||
| 書誌情報 |
Bulletin of the Chemical Society of Japan 巻 67, 号 9, p. 2383-2387, 発行日 1994 |
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| ISSN | ||||||
| 収録物識別子タイプ | ISSN | |||||
| 収録物識別子 | 00092673 | |||||
| 書誌レコードID | ||||||
| 収録物識別子タイプ | NCID | |||||
| 収録物識別子 | AA00580132 | |||||
| DOI | ||||||
| 関連タイプ | isIdenticalTo | |||||
| 識別子タイプ | DOI | |||||
| 関連識別子 | 10.1246/bcsj.67.2383 | |||||
| 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 | |||||
| 出版者 | ||||||
| 出版者 | Chemical Society of Japan | |||||
| 出版者（他言語） | ||||||
| 値 | 日本化学会 | |||||
