Solvent-induced chirality switching in the enantioseparation of regioisomeric hydroxyphenylpropionic acids via diastereomeric salt formation with (1R,2S)-2-amino-1,2-diphenylethanol |
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Authors: | Koichi Kodama Jun Nagata Nobuhiro Kurozumi Hiroaki Shitara Takuji Hirose |
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Institution: | 1. Graduate School of Science and Engineering, Saitama University, 255 Shimo-Okubo, Sakura-ku, Saitama 338-8570, Japan;2. Technical Support Center, Saitama University, 255 Shimo-Okubo, Sakura-ku, Saitama 338-8570, Japan |
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Abstract: | The enantioseparation of three hydroxyphenylpropionic acid isomers via diastereomeric salt formation with (1R,2S)-2-amino-1,2-diphenylethanol has been demonstrated. The racemates of all three acid isomers were successfully separated with high efficiency (0.56–0.84) after single crystallization. For 2-hydroxy-3-phenylpropionic acid 4, the configuration of the less-soluble salt was controlled by the crystallization solvent: the (R)-4 salt was crystallized from water, while 2-propanol afforded the (S)-4 salt. The chiral recognition mechanism of the three acids was discussed based on the crystal structures of the diastereomeric salts. |
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Keywords: | Corresponding authors Tel /fax: +81 48 858 9548 |
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