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タイトル: Synthesis of enantiopure 6-methoxy-2-naphthylglycolic acid and its application as a resolving agent
著者: Saigo, Kazuhiko
Shimada, Takayoshi
Kobayashi, Yuka
発行日: 2005年11月28日
出版者: Elsevier
掲載誌情報: Tetrahedron: Asymmetry. 16(23), 2005.11, pp. 3807-3813
関連URI: http://www.elsevier.com/locate/issn/09574166
抄録: 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.
URI: http://hdl.handle.net/2261/6006
ISSN: 09574166
出現カテゴリ:014 自然科学
1134010 学術雑誌論文


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