Macrocyclic chiral receptors toward enantioselective recognition of naproxen.
[structure: see text] A macrocyclic receptor based on a bischromenylurea and an alpha,alpha'-(o,o'-dialkyl)diphenyl-p-xylylenediamine spacer provides a C(2) chiral cavity to associate carboxylates by H-bonds. The extent of the selectivity obtained for the racemic receptor 2 and enantiomerically pure (S)-naproxen is 7.2:1. Steric repulsions close to the cavity are decisive for the chiral selectivity.
Gonzalez
Silvia
S
Departamento de Química Organica, Universidad de Salamanca, Plaza de los Caídos 1-5, 37008 Salamanca, Spain.
Pelaez
Rafael
R
Sanz
Francisca
F
Jiménez
M Belén
MB
Moran
Joaquín R
JR
Caballero
M Cruz
MC
D001665:Binding Sites; D018360:Crystallography, X-Ray; D008968:Molecular Conformation; D015394:Molecular Structure; D009288:Naproxen / Q000737:chemistry*; D013237:Stereoisomerism; D014508:Urea / Q000031:analogs & derivatives* / Q000737:chemistry*; D014992:Xylenes / Q000737:chemistry*
D014992:Xylenes; D009288:Naproxen; D014508:Urea