Scalable Enantiomeric Separation of Dialkyl-Arylphosphine Oxides Based on Host–Guest Complexation with TADDOL-Derivatives, and their Recovery
KAUST DepartmentAdvanced Membranes and Porous Materials Research Center
Chemical Engineering Program
Physical Science and Engineering (PSE) Division
Online Publication Date2020-03-13
Print Publication Date2020-03-31
Permanent link to this recordhttp://hdl.handle.net/10754/662292
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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.
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
SponsorsThis 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.
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