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

Martina Palomino-Schätzlein, Albert Virgili, Sergio Gil, Carlos Jaime

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22 Citations (Scopus)

Abstract

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.
Original languageEnglish
Pages (from-to)8114-8120
JournalJournal of Organic Chemistry
Volume71
Issue number21
DOIs
Publication statusPublished - 13 Oct 2006

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