Synthesis of enantiopure 6-methoxy-2-naphthylglycolic acid and its application as a resolving agent

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概要

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• 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.

• Elsevierの論文
• 2005-11-28

著者

• Saigo Kazuhiko

  Dep. Of Chemistry And Biotechnology Graduate School Of Engineering The Univ. Of Tokyo Hongo Bunkyo-k

関連論文

• Synthesis of enantiopure 6-methoxy-2-naphthylglycolic acid and its application as a resolving agent

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