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This article is dedicated to Prof. Josep Font Cierco (UAB) on the occasion of his 70th birthday.
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Regular Article
Molecular tweezers for enantiodiscrimination in NMR: Di-(R,R)-1-[10-(1-hydroxy-2,2,2-trifluoroethyl)-9-anthryl]-2,2,2-trifluoroethyl benzenedicarboxylates†
Article first published online: 2 NOV 2009
DOI: 10.1002/chir.20786
Copyright © 2009 Wiley-Liss, Inc.
Additional Information
How to Cite
Gil, S., Palomino-Schätzlein, M., Burusco, K. K., Jaime, C. and Virgili, A. (2010), Molecular tweezers for enantiodiscrimination in NMR: Di-(R,R)-1-[10-(1-hydroxy-2,2,2-trifluoroethyl)-9-anthryl]-2,2,2-trifluoroethyl benzenedicarboxylates. Chirality, 22: 548–556. doi: 10.1002/chir.20786
- †
Publication History
- Issue published online: 23 APR 2010
- Article first published online: 2 NOV 2009
- Manuscript Accepted: 4 AUG 2009
- Manuscript Received: 7 MAY 2009
Funded by
- Universitat Autònoma de Barcelona (Ministerio de Educación y Ciencia de España). Grant Number: CYCYT (CTQ2006-01080)
Keywords:
- chiral solvating agents;
- enantiodiscrimination;
- NMR;
- enantiomeric excess;
- molecular tweezers
Abstract
A series of new chiral molecular tweezers, di-(R,R)-1-[10-(1-hydroxy-2,2,2-trifluoroethyl)-9-anthryl]-2,2,2-trifluoroethyl phthalate (2), isophthalate (3) and terephthalate (4), were synthesized and their structure studied by NMR and molecular mechanics. Their effectiveness as chiral solvating agents for the determination of the enantiomeric purity of chiral compounds using NMR was demonstrated. Chirality 2010. © 2009 Wiley-Liss, Inc.