Enantioseparation of α‐Hydroxyallylphosphonates and Phosphonoallylic Carbonate Derivatives on Chiral Stationary Phases Using Sequential UV,Polarimetric, and Refractive Index Detection |
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| Authors: | Bruce C Hamper Michael P Mannino Melissa E Mueller Liam T Harrison Christopher D Spilling |
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| Affiliation: | Department of Chemistry and Biochemistry, University of Missouri‐St. Louis, St. Louis, Missouri, USA |
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| Abstract: | Chromatographic separation of the enantiomers of parent compounds dimethyl α‐hydroxyallyl phosphonate 1a and 1‐(dimethoxyphosphoryl) allyl methyl carbonate 1b was demonstrated by high‐performance liquid chromatography (HPLC) using Chiralpak AS‐H and ad ‐H chiral stationary phases (CSP), respectively, using a combination of UV, polarimetric, and refractive index detectors. A comparison was made of the separation efficiency and elution order of enantiomeric α‐hydroxyallyl phosphonates and their carbonate derivatives on commercially available polysaccharide AS, ad , OD, IC‐3, and Whelk‐O 1 CSPs. In general, the α‐hydroxyallyl phosphonates were resolved on the AS‐H CSP, whereas the carbonate derivatives 1b and 2b were preferentially resolved on the ad ‐H CSP. The impact of aryl substitution on the resolution of analytes 1d , 1e , 1f and 2 , 3 , 4 , 5 , 6 , 7 , 8 was evaluated. Thermodynamic parameters determined for enantioselective adsorption hydroxyphosphonates 1a and 4 on the AS‐H CSP and carbonate 1b on the ad ‐H CSP demonstrated enthalpic control for separation of the enantiomers. Chirality 28:656–662, 2016. © 2016 Wiley Periodicals, Inc. |
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| Keywords: | α ‐hydroxy phosphonates chiral stationary phases enantiomer separation HPLC multiple detectors phosphonoallylic carbonates polarimetric detection |
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