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.
