TY - JOUR
T1 - Scalable Enantiomeric Separation of Dialkyl-Arylphosphine Oxides Based on Host–Guest Complexation with TADDOL-Derivatives, and their Recovery
AU - Varga, Bence
AU - Herbay, Réka
AU - Szekely, Gyorgy
AU - Holczbauer, Tamás
AU - Madarász, János
AU - Mátravölgyi, Béla
AU - Fogassy, Elemér
AU - Keglevich, György
AU - Bagi, Péter
N1 - KAUST Repository Item: Exported on 2020-10-01
Acknowledgements: This 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.
PY - 2020/2/10
Y1 - 2020/2/10
N2 - Several 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.
AB - Several 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.
UR - http://hdl.handle.net/10754/662292
UR - http://doi.wiley.com/10.1002/ejoc.202000035
UR - http://www.scopus.com/inward/record.url?scp=85081727267&partnerID=8YFLogxK
U2 - 10.1002/ejoc.202000035
DO - 10.1002/ejoc.202000035
M3 - Article
VL - 2020
SP - 1840
EP - 1852
JO - European Journal of Organic Chemistry
JF - European Journal of Organic Chemistry
SN - 1434-193X
IS - 12
ER -