TY - JOUR
T1 - Di-(R,R)-1-[10-(1-hydroxy-2,2,2-trifluoroethyl)-9-anthryl]-2,2, 2-trifluoroethyl muconate: A highly chiral cavity for enantiodiscrimination by NMR
AU - Palomino-Schätzlein, Martina
AU - Virgili, Albert
AU - Gil, Sergio
AU - Jaime, Carlos
PY - 2006/10/13
Y1 - 2006/10/13
N2 - A new chiral molecular tweezer, di-(R,R)-1-[10-(1-hydroxy-2,2,2- trifluoroethyl)-9-anthryl]-2,2,2-trifluoroethyl muconate 2, was synthesized in enantiopure form, and its geometry was studied using NMR and molecular mechanics. The effectiveness of 2 as a chiral solvating agent for determining the enantiomeric composition of chiral compounds using NMR was demonstrated, improving the results obtained with other methods. The stoichiometry and the association constant of the resulting diastereomeric complexes were studied, and their geometry was analyzed by NOE and 1H NMR. © 2006 American Chemical Society.
AB - A new chiral molecular tweezer, di-(R,R)-1-[10-(1-hydroxy-2,2,2- trifluoroethyl)-9-anthryl]-2,2,2-trifluoroethyl muconate 2, was synthesized in enantiopure form, and its geometry was studied using NMR and molecular mechanics. The effectiveness of 2 as a chiral solvating agent for determining the enantiomeric composition of chiral compounds using NMR was demonstrated, improving the results obtained with other methods. The stoichiometry and the association constant of the resulting diastereomeric complexes were studied, and their geometry was analyzed by NOE and 1H NMR. © 2006 American Chemical Society.
U2 - 10.1021/jo061276d
DO - 10.1021/jo061276d
M3 - Article
SN - 0022-3263
VL - 71
SP - 8114
EP - 8120
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
IS - 21
ER -