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Title
| - The Assignment of the Absolute Configuration of Diethyl Hydroxy-and Aminophosphonates by 1H and 31P NMR Using Naproxen as aReliable Chiral Derivatizing Agent
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Abstract
| - The assignment of the absolute configuration of hydroxy- and aminophosphonates by their doublederivatization with commercially available naproxen is presented. The correlation between the spatialarrangement around the stereogenic carbon center and the signs of the ΔδRS allows determination of theabsolute configuration of hydroxy- and aminophosphonates by simple comparison of the 1H and 31PNMR 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 structurallydiverse naproxen esters and amides of hydroxy- and aminophosphonates proved that a simplified modelcan be successfully used.
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