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Figure 5. 1H NMR spectra (400 MHz, 8% acetone-d6/CDCl3,
22°C, parts) of [5c][D-3]2, d.e. ꢀ36%.
5. (a) Lacour, J.; Ginglinger, C.; Favarger, F.; Torche-
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Lacour, J.; Jodry, J. J.; Ginglinger, C.; Torche-Haldi-
mann, S. Angew. Chem., Int. Ed. Engl. 1998, 37, 2379–
2380; (c) Lacour, J.; Goujon-Ginglinger, C.;
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Rose, E.; Monchaud, D.; Lacour, J. Organometallics
2001, 20, 4107–4110.
6. Lacour, J.; Londez, A.; Goujon-Ginglinger, C.; Buß, V.;
Bernardinelli, G. Org. Lett. 2000, 2, 4185–4188.
7. Lacour, J.; Londez, A. J. Organomet. Chem. 2001, in
press.
8. (a) Giner Planas, J.; Prim, D.; Rose-Munch, F.; Rose, E.;
Monchaud, D.; Lacour, J. Organometallics 2001, 20,
4107–4110; (b) Monchaud, D.; Lacour, J.; Coudret, C.;
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Ref. 5e.
In conclusion, association of chiral diquats and hexaco-
ordinated phosphate anions was realized and yielded
the first example of configurational ordering of these
cationic species. Importantly, we have observed that the
overall symmetry of the chiral anion (D3 or C2) is not
as important as the resulting solubility of the ion pair;
anion 4 in spite of its C2-symmetry is less efficient than
TRISPHAT 2. Nevertheless, C2-symmetric BINPHAT
anion remains the most efficient asymmetric inducting
agent.
Acknowledgements
We thank the Swiss National Science Foundation, the
Federal Office for Education and Science (COST D11
Supramolecular Chemistry WG 003/98, J.L., C.P.), and
the ‘Fondation de Famille Sandoz’ for a professorship
(J.L.) and a post-doctoral fellowship (V.D.B.).
9. The relationship DG"=RTc (22.96+ln(Tc/ꢀ(Dw2+6J2))
was used to determine the activation energy, DG", from
the coalescence temperature, Tc (K), the frequency sepa-
ration of the peaks, Dw (Hz), and the coupling constant
between the nuclei, J (Hz).
10. Lacour, J.; Barche´chath, S.; Jodry, J. J.; Ginglinger, C.
Tetrahedron Lett. 1998, 39, 567–570.
11. Chemical shifts for each enantiomer of salt [5b][(R,R)-4]2
were assigned using COSY experiments and revealed
upfield or downfield shifts induced by the phosphate
reagent.
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