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Synthesis of enantiopure 6-methoxy-2-naphthylglycolic acid and its application as a resolving agent
http://hdl.handle.net/2261/6006
http://hdl.handle.net/2261/6006dd531bb0-a555-4c68-aedf-613e25afeba0
| 名前 / ファイル | ライセンス | アクション |
|---|---|---|
15_Elsevier_w.pdf (265.1 kB)
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| Item type | 学術雑誌論文 / Journal Article(1) | |||||
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| 公開日 | 2007-05-10 | |||||
| タイトル | ||||||
| タイトル | Synthesis of enantiopure 6-methoxy-2-naphthylglycolic acid and its application as a resolving agent | |||||
| 言語 | ||||||
| 言語 | eng | |||||
| 資源タイプ | ||||||
| 資源 | http://purl.org/coar/resource_type/c_6501 | |||||
| タイプ | journal article | |||||
| 著者 |
Saigo, Kazuhiko
× Saigo, Kazuhiko× Shimada, Takayoshi× Kobayashi, Yuka |
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| 抄録 | ||||||
| 内容記述タイプ | Abstract | |||||
| 内容記述 | As a novel acidic resolving agent, 6-methoxy-2-naphthylglycolic acid (6-MNGA) was designed on the model of 2-naphthylglycolic acid (2-NGA). Enantiopure 6-MNGA was easily obtained from commercially available 2-bromo-6-methoxynaphthalene through four steps and was found to show a better chiral recognition ability for racemic 1-arylethylamines than did the prototype 2-NGA. The X-ray crystallographic analyses of the less-soluble diastereomeric salts revealed that the introduction of a methoxy group at the 6-position of the 2-NGA skeleton made CH/interaction(s) effective between 6-MNGA molecules and between 6-MNGA molecule and the target amine molecule. The methoxy group was also found to contribute to the realization of effective van der Waals interaction. These interactions played important roles for the stabilization of the less-soluble diastereomeric salts to improve the chiral recognition ability of 6-MNGA, compared to that of 2-NGA. | |||||
| 書誌情報 |
Tetrahedron: Asymmetry 巻 16, 号 23, p. 3807-3813, 発行日 2005-11-28 |
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| ISSN | ||||||
| 収録物識別子タイプ | ISSN | |||||
| 収録物識別子 | 09574166 | |||||
| DOI | ||||||
| 識別子タイプ | DOI | |||||
| 関連識別子 | info:doi/10.1016/j.tetasy.2005.10.019 | |||||
| フォーマット | ||||||
| 内容記述タイプ | Other | |||||
| 内容記述 | application/pdf | |||||
| 著者版フラグ | ||||||
| 値 | author | |||||
| 出版者 | ||||||
| 出版者 | Elsevier | |||||
| 関係URI | ||||||
| 識別子タイプ | URI | |||||
| 関連識別子 | http://www.elsevier.com/locate/issn/09574166 | |||||
