Racemic N-arylamino-1-arylmethylphosphonic acid diethyl esters with various fluorinated substituents in one or both aryl rings have been resolved in their enantiomers by a direct HPLC method, using chiral stationary phases. The chiral separation on Chiralcel OD strongly depends on the substitution pattern in the N-aryl and/or in the C-aryl moieties and it improves markedly with the polarity of the fluorinated substituent. A new Pirkle's chiral stationary phase (R)-alpha-Burke 1 is more efficient and in some cases more enantioselective than other Pirkle's phases. A chiral recognition model between this phase and the enantiomers of an analyte afforded to propose the absolute configuration of the optical isomers and to relate it to the chiroptical behaviour.
DIRECT CHIRAL HPLC SEPARATION OF THE ENANTIOMERS OF FLUORINATED N-ARYLAMINO-1-ARYLMETHYLPHOSPHONATE ESTERS - SUBSTITUENT EFFECTS ON THE ENANTIOSELECTIVITY
FAILLA, Salvatore
1994-01-01
Abstract
Racemic N-arylamino-1-arylmethylphosphonic acid diethyl esters with various fluorinated substituents in one or both aryl rings have been resolved in their enantiomers by a direct HPLC method, using chiral stationary phases. The chiral separation on Chiralcel OD strongly depends on the substitution pattern in the N-aryl and/or in the C-aryl moieties and it improves markedly with the polarity of the fluorinated substituent. A new Pirkle's chiral stationary phase (R)-alpha-Burke 1 is more efficient and in some cases more enantioselective than other Pirkle's phases. A chiral recognition model between this phase and the enantiomers of an analyte afforded to propose the absolute configuration of the optical isomers and to relate it to the chiroptical behaviour.I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
