Enantioseparation of racemic N-acylarylalkylamines on various amino alcohol derived tau-acidic chiral stationary phases |
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Authors: | Ryoo Jae Jeong Kim Tae Hyuk Im Sung Hyun Jeong Young Han Park Ji Yeon Choi Seong-Ho Lee Kwang-Pill Park Jung Hag |
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Institution: | Department of Chemistry, Graduate School, Kyungpook National University, 1370 Sankyuk-Dong, Buk-Ku, Taegu 702-701, South Korea. jjryoo@knu.ac.kr |
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Abstract: | Five tau-acidic chiral stationary phases (CSPs), CSP 4, CSP 5, CSP 6, CSP 7 and CSP 8, were prepared by connecting the N-(3,5-dimethylbenzoyl) derivative of (R)-alaninol, (S)-leucinol, (1S,2R)-ephedrine and (S)-tert-leucinol and the O-(3,5-dinitrobenzoyl) derivative of (R)-phenylglycinol to silica gel through a carbamate or urea linkage. The CSPs were applied to the resolution of various racemic N-acyl-1-naphthylaminoalkanes by chiral HPLC, and the chromatographic resolution results were compared with those of previously reported CSPs (CSP 2, CSP 3), which are derived from N-(3,5-dinitrobenzoyl)-(1S,2R)-norephedrine and N-(3,5-dinitrobenzoyl-(R)-phenylglycinol. Based on a comparison of the resolution results for each CSP, the role of each functional group on the five chiral selectors is explained. |
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