Abstract
The use of quinine as a chiral solvating agent allows us to determine a tentative absolute configuration at the phosphorus atom of hydroxyphosphinates with two stereogenic centres (at the phosphorus and α-carbon atoms). Two ethyl butyryloxyalkane( P-phenyl)phosphinates were hydrolysed using various lipases. In all cases isomers possessing α-carbon atom with an ( S)-configuration were hydrolysed preferentially. The absolute configuration of both chiral centres of obtained α-hydroxyphosphinates was determined by using ( S)-(+)-MTPA-Cl and quinine. The mode of chiral discrimination of α-hydroxyphosphinates by quinine was studied by means of computational chemistry, which confirmed the experimental findings that the signals in 31P NMR spectra of compounds with an ( R P)-configuration are situated upfield when compared with the respective ( S P) isomers.
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