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Bulletin of the Korean Chemical Society (BKCS)

ISSN 0253-2964(Print)
ISSN 1229-5949(Online)
Volume 16, Number 8
BKCSDE 16(8)
August 20, 1995 

Resolution of Amide Derivatives of Naproxen on Pirkle-Type π-Acidic Chiral Stationary Phases
Myung Ho Hyun*, Yoon Jae Cho, Chung Sik Min, Jae-Jeong Ryoo
A chiral recognition model which explains the chiral resolution behavior of N-alkyl amide derivatives of naproxen on the Pirkle type π -acidic CSPs derived from N-(3,5-dinitrobenzoyl)-(R)-phenylglycine and N-(3,5-dinitrobenzoyl)-(S)-leucine has been proposed. Based on the proposed model, an effort to improve the resolution of racemic naproxen derivatives on the CSP has been devoted and consequently, N-alkyl N-aryl amides of naproxen or N-alkyl N-cyclohexyl amides of naproxen have been found to be resolved quite well on a Pirkle type π-acidic CSP. Based on the reciprocity conception of chiral recognition, CSPs which might show excellent resolving ability for π-acidic racemic compounds have been suggested.
764 - 768
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