The effects of aromatic substituents on the chromatographic enantioseparation of diarylmethyl esters with the Whelk-O1 chiral stationary phase
| Autor: | Nobuyuki Harada, Masataka Watanabe, Yusuke Kasai, Alex Shvets, William H. Pirkle, Masashi Kosaka, Kaori Fujita, Gabriel E. Job, Shunsuke Kuwahara, Hiromi Taji |
|---|---|
| Rok vydání: | 2004 |
| Předmět: |
Magnetic Resonance Spectroscopy
Chromatography Chemistry Organic Chemistry Esters Stereoisomerism General Medicine Chiral stationary phase Biochemistry High-performance liquid chromatography Analytical Chemistry Chiral column chromatography Hydrolysis Proton NMR High field Enantiomer Chromatography High Pressure Liquid |
| Zdroj: | Journal of Chromatography A. 1055:41-53 |
| ISSN: | 0021-9673 |
| DOI: | 10.1016/j.chroma.2004.08.001 |
| Popis: | Members of a series of diarylmethanols, diarylmethyl pivalates, and diarylmethyl acetates (analyte sets 1-26) were enantioresolved with the (S,S)-Whelk-O1 chiral stationary phase (CSP). An analogue of the (S,S)-Whelk-O1 selector was combined with enantioenriched samples of the various diarylmethyl pivalates and thereby used as a chiral solvating agent (CSA) for high field 1H NMR studies. The absolute configurations of a number of chiral diarylmethyl pivalates were assigned using this approach, and hydrolysis of the pivalates allowed assignment of the absolute configurations of the corresponding diarylmethanols. Chromatographic, 1H NMR, and X-ray evidence are given in support of a chiral recognition model for the enantioresolution of diarylmethyl esters on this CSP. |
| Databáze: | OpenAIRE |
| Externí odkaz: |
|
Full Text from ScienceDirect