2227-43-2Relevant articles and documents
Scalable Enantiomeric Separation of Dialkyl-Arylphosphine Oxides Based on Host–Guest Complexation with TADDOL-Derivatives, and their Recovery
Bagi, Péter,Fogassy, Elemér,Herbay, Réka,Holczbauer, Tamás,Keglevich, Gy?rgy,Mátrav?lgyi, Béla,Madarász, János,Székely, Gy?rgy,Varga, Bence
, (2020/03/23)
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.
Resolution of chiral phosphate, phosphonate, and phosphinate esters by an enantioselective enzyme library
Nowlan, Charity,Li, Yingchun,Hermann, Johannes C.,Evans, Timothy,Carpenter, Joseph,Ghanem, Eman,Shoichet, Brian K.,Raushel, Frank M.
, p. 15892 - 15902 (2007/10/03)
An array of 16 enantiomeric pairs of chiral phosphate, phosphonate, and phosphinate esters was used to establish the breadth of the stereoselective discrimination inherent within the bacterial phosphotriesterase and 15 mutant enzymes. For each substrate,
Trimethylsilyl halide-promoted Michaelis-Arbuzov rearrangement
Renard, Pierre-Yves,Vayron, Philippe,Mioskowski, Charles
, p. 1661 - 1664 (2007/10/03)
(Matrix presented) We describe a new, straightforward, and easy-to-handle method for achieving an unprecedented trimethylsilyl halide-catalyzed Michaelis-Arbuzov-like rearrangement. This rearrangement occurs at temperatures from room temperature to 80°C and does not require addition of any alkyl halide. The scope and limitations of this new reaction are explored, as well as its mechanism.
