The assignment of the absolute configuration of diethyl hydroxy- and aminophosphonates by 1H and 31P NMR using naproxen as a reliable chiral derivatizing agent.
The assignment of the absolute configuration of hydroxy- and aminophosphonates by their double derivatization with commercially available naproxen is presented. The correlation between the spatial arrangement around the stereogenic carbon center and the signs of the DeltadeltaRS allows determination of the absolute configuration of hydroxy- and aminophosphonates by simple comparison of the 1H and 31P NMR spectra of the (R)- and (S)-naproxen ester or amide derivatives. Extensive conformational analysis (theoretical calculations, low-temperature experiments) supported by the NMR studies of structurally diverse naproxen esters and amides of hydroxy- and aminophosphonates proved that a simplified model can be successfully used.
Błazewska
Katarzyna
K
The Faculty of Chemistry, Technical University of Lodz (Politechnika), Zeromskiego St. 116, 90-924 Lodz, Poland.
Paneth
Piotr
P
Gajda
Tadeusz
T
D000465:Algorithms; D000577:Amides / Q000737:chemistry; D002244:Carbon / Q000737:chemistry; D004952:Esters / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy / Q000379:methods; D008968:Molecular Conformation; D009288:Naproxen / Q000737:chemistry*; D063065:Organophosphonates / Q000737:chemistry*; D009943:Organophosphorus Compounds / Q000737:chemistry*; D013237:Stereoisomerism; D013696:Temperature
D000577:Amides; D004952:Esters; D063065:Organophosphonates; D009943:Organophosphorus Compounds; D009288:Naproxen; D002244:Carbon