Efficient NMR enantiodiscrimination of bridge fluorinated paracyclophanes using lanthanide tris β-diketonate complexes

Alex J. Roche, Sheryl A. Rabinowitz, Kasey A. Cox

Research output: Contribution to journalArticlepeer-review

5 Scopus citations

Abstract

A selection of amino-substituted 1,1,2,2,9,9,10,10 octafluoro[2.2] paracyclophanes were tested for enantiodiscrimination by 1H and 19F NMR spectroscopy via their interaction with different lanthanide tris β-diketonate chiral shift reagents. The amino-, and the pseudo-ortho di-amino substituted octafluoro[2.2]paracyclophanes, both of which exhibit planar chirality, revealed significant shifts and splittings of various 1H and 19F NMR signals upon the addition of the chiral shift reagents, which allowed the easy determination of the enantiomeric purity. When the chiral shift reagent was added to an inseparable mixture of the (chiral) pseudo-meta, and (achiral) pseudo-para diamino analogues, both the chiral and achiral molecules revealed NMR doubling. In the case of the achiral molecule, this NMR behavior is due to the meso nature of the pseudo-para species.

Original languageEnglish (US)
Pages (from-to)1382-1388
Number of pages7
JournalTetrahedron Asymmetry
Volume24
Issue number21-22
DOIs
StatePublished - Nov 30 2013

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Physical and Theoretical Chemistry
  • Organic Chemistry
  • Inorganic Chemistry

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