Enantioseparation of α‐Hydroxyallylphosphonates and Phosphonoallylic Carbonate Derivatives on Chiral Stationary Phases Using Sequential UV, Polarimetric, and Refractive Index Detection

作者: Bruce C. Hamper , Michael P. Mannino , Melissa E. Mueller , Liam T. Harrison , Christopher D. Spilling

DOI: 10.1002/CHIR.22627

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摘要: Chromatographic separation of the enantiomers parent compounds dimethyl α-hydroxyallyl phosphonate and 1-(dimethoxyphosphoryl) allyl methyl carbonate was demonstrated by high-performance liquid chromatography (HPLC) using Chiralpak AS-H ad-H chiral stationary phases (CSP), respectively, a combination UV, polarimetric, refractive index detectors. A comparison made efficiency elution order enantiomeric phosphonates their derivatives on commercially available polysaccharide AS, ad, OD, IC-3, Whelk-O 1 CSPs. In general, were resolved CSP, whereas preferentially CSP. The impact aryl substitution resolution analytes evaluated. Thermodynamic parameters determined for enantioselective adsorption hydroxyphosphonates CSP enthalpic control enantiomers. Chirality 28:656-662, 2016. © 2016 Wiley Periodicals, Inc.

参考文章(25)
Anyu He, Nongnuch Sutivisedsak, Christopher D Spilling, None, Stereoselective Synthesis of Cyclic Ethers via the Palladium-Catalyzed Intramolecular Addition of Alcohols to Phosphono Allylic Carbonates Organic Letters. ,vol. 11, pp. 3124- 3127 ,(2009) , 10.1021/OL900980S
Fei Yang, Dongbing Zhao, Jingbo Lan, Peihua Xi, Li Yang, Shuhuai Xiang, Jingsong You, Self-assembled bifunctional catalysis induced by metal coordination interactions: an exceptionally efficient approach to enantioselective hydrophosphonylation. Angewandte Chemie. ,vol. 47, pp. 5646- 5649 ,(2008) , 10.1002/ANIE.200801766
Ab.A. Smaardijk, Simon Noorda, Fré van Bolhuis, Hans Wynberg, The absolute configuration of α-hydroxyphosphonates Tetrahedron Letters. ,vol. 26, pp. 493- 496 ,(1985) , 10.1016/S0040-4039(00)61920-2
Ewa Żymańczyk-Duda, Mariusz Skwarczyński, Barbara Lejczak, Pawel Kafarski, Accurate assay of enantiopurity of 1-hydroxy- and 2-hydroxyalkylphosphonate esters Tetrahedron-asymmetry. ,vol. 7, pp. 1277- 1280 ,(1996) , 10.1016/0957-4166(96)00143-7
Sudeshna Roy, Christopher D. Spilling, An expeditious total synthesis of both diastereoisomeric lipid dihydroxytetrahydrofurans from Notheia anomala. Organic Letters. ,vol. 14, pp. 2230- 2233 ,(2012) , 10.1021/OL300597U
Torgny Fornstedt, Peter Sajonz, Georges Guiochon, Thermodynamic Study of an Unusual Chiral Separation. Propranolol Enantiomers on an Immobilized Cellulase Journal of the American Chemical Society. ,vol. 119, pp. 1254- 1264 ,(1997) , 10.1021/JA9631458
Sudeshna Roy, Christopher D. Spilling, Synthesis of the C(18)−C(34) Fragment of Amphidinolide C and the C(18)−C(29) Fragment of Amphidinolide F Organic Letters. ,vol. 12, pp. 5326- 5329 ,(2010) , 10.1021/OL102345V
Hans Wynberg, Ab A. Smaardijk, Asymmetric catalysis in carbon-phosphorus bond formation Tetrahedron Letters. ,vol. 24, pp. 5899- 5900 ,(1983) , 10.1016/S0040-4039(00)94232-1
Bingli Yan, Christopher D. Spilling, Stereospecific Pd(O)-catalyzed malonate additions to allylic hydroxy phosphonate derivatives: a formal synthesis of (-)-enterolactone. Journal of Organic Chemistry. ,vol. 69, pp. 2859- 2862 ,(2004) , 10.1021/JO035795H