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dc.contributor.authorVarga, Bence
dc.contributor.authorHerbay, Réka
dc.contributor.authorSzekely, Gyorgy
dc.contributor.authorHolczbauer, Tamás
dc.contributor.authorMadarász, János
dc.contributor.authorMátravölgyi, Béla
dc.contributor.authorFogassy, Elemér
dc.contributor.authorKeglevich, György
dc.contributor.authorBagi, Péter
dc.date.accessioned2020-03-25T08:09:11Z
dc.date.available2020-03-25T08:09:11Z
dc.date.issued2020-03-13
dc.date.submitted2020-01-10
dc.identifier.citationVarga, B., Herbay, R., Székely, G., Holczbauer, T., Madarász, J., Mátravölgyi, B., … Bagi, P. (2020). Scalable Enantiomeric Separation of Dialkyl-Arylphosphine Oxides Based on Host-Guest Complexation with TADDOL-Derivatives, and their Recovery. European Journal of Organic Chemistry, 2020(12), 1840–1852. doi:10.1002/ejoc.202000035
dc.identifier.doi10.1002/ejoc.202000035
dc.identifier.urihttp://hdl.handle.net/10754/662292
dc.description.abstractSeveral dialkyl-arylphosphine oxides were prepared, and the enantioseparation of the corresponding racemates was elaborated with host–guest complexation using TADDOL-derivatives. The crystallization conditions were optimized and two separate crystallization methods, one in organic solvent, and the other in water, were found to yield five examples of phosphine oxides with enantiomeric excess values higher than 94 %. A gram scale resolution was performed, and both enantiomers of the methyl-phenyl-propyl-phosphine oxide were separated with (R,R)- or (S,S)-spiro-TADDOL. The intermolecular interactions responsible for the enantiomeric recognition between the chiral host and guest molecules were investigated by single-crystal X-ray diffractional structural determinations. The similarities in the structural patterns of a few diastereomeric crystals were checked by powder X-ray diffraction, as well. Organic solvent nanofiltration (OSN) was used as a scalable technique for the decomposition of the corresponding phosphine oxide–spiro-TADDOL molecular complexes, and for the recovery of the phosphine oxide enantiomers and resolving agents.
dc.description.sponsorshipThis work was supported by the National Research, Development and Innovation Office - NKFIH (Grant No. OTKA PD 116096). Tamás Holczbauer is grateful for the support of the National Research, Development and Innovation Office-NKFIH (Grant No. OTKA PD 128504) and the János Bolyai Research Scholarship of the HAS. György Székely acknowledges the financial support from KAUST.
dc.publisherWiley
dc.relation.urlhttp://doi.wiley.com/10.1002/ejoc.202000035
dc.rightsThis is an open access article under the terms of the Creative Commons Attribution-NonCommercial-NoDerivs License, which permits use and distribution in any medium, provided the original work is properly cited, the use is non-commercial and no modifications or adaptations are made.
dc.rights.urihttp://creativecommons.org/licenses/by-nc-nd/4.0/
dc.titleScalable Enantiomeric Separation of Dialkyl-Arylphosphine Oxides Based on Host–Guest Complexation with TADDOL-Derivatives, and their Recovery
dc.typeArticle
dc.contributor.departmentAdvanced Membranes and Porous Materials Research Center
dc.contributor.departmentChemical Engineering Program
dc.contributor.departmentPhysical Science and Engineering (PSE) Division
dc.identifier.journalEuropean Journal of Organic Chemistry
dc.eprint.versionPublisher's Version/PDF
dc.contributor.institutionDepartment of Organic Chemistry and Technology, Budapest University of Technology and Economics, Műegyetem rkp. 3., 1111, Budapest, Hungary
dc.contributor.institutionDepartment of Chemical Engineering and Analytical Science, The University of Manchester, The Mill, Sackville Street, M1 3BB, Manchester, United Kingdom
dc.contributor.institutionChemical Crystallography Research Laboratory and Institute of Organic Chemistry, Research Centre for Natural Sciences, Magyar tudósok körútja 2., 1519, Budapest, Hungary
dc.contributor.institutionDepartment of Inorganic and Analytical Chemistry, Budapest University of Technology and Economics, Szent Gellért tér 4., 1111, Budapest, Hungary
kaust.personSzekely, Gyorgy
dc.date.accepted2020-02-09
dc.relation.issupplementedbyDOI:10.5517/ccdc.csd.cc23pv7x
dc.relation.issupplementedbyDOI:10.5517/ccdc.csd.cc23pv6w
refterms.dateFOA2020-03-25T08:12:02Z
display.relations<b> Is Supplemented By:</b> <br/> <ul> <li><i>[Dataset]</i> <br/> . DOI: <a href="https://doi.org/10.5517/ccdc.csd.cc23pv7x">10.5517/ccdc.csd.cc23pv7x</a> HANDLE: <a href="http://hdl.handle.net/10754/664872">10754/664872</a></li></ul><b> Is Supplemented By:</b> <br/> <ul> <li><i>[Dataset]</i> <br/> . DOI: <a href="https://doi.org/10.5517/ccdc.csd.cc23pv7x">10.5517/ccdc.csd.cc23pv7x</a> HANDLE: <a href="http://hdl.handle.net/10754/664873">10754/664873</a></li></ul><b> Is Supplemented By:</b> <br/> <ul> <li><i>[Dataset]</i> <br/> . DOI: <a href="https://doi.org/10.5517/ccdc.csd.cc23pv7x">10.5517/ccdc.csd.cc23pv7x</a> HANDLE: <a href="http://hdl.handle.net/10754/664874">10754/664874</a></li></ul><b> Is Supplemented By:</b> <br/> <ul> <li><i>[Dataset]</i> <br/> . DOI: <a href="https://doi.org/10.5517/ccdc.csd.cc23pv6w">10.5517/ccdc.csd.cc23pv6w</a> HANDLE: <a href="http://hdl.handle.net/10754/664875">10754/664875</a></li></ul>
dc.date.published-online2020-03-13
dc.date.published-print2020-03-31


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This is an open access article under the terms of the Creative Commons Attribution-NonCommercial-NoDerivs License, which permits use and distribution in any medium, provided the original work is properly cited, the use is non-commercial and no modifications or adaptations are made.
Except where otherwise noted, this item's license is described as This is an open access article under the terms of the Creative Commons Attribution-NonCommercial-NoDerivs License, which permits use and distribution in any medium, provided the original work is properly cited, the use is non-commercial and no modifications or adaptations are made.