4 T. R. Chan, R. Hilgraf, K. B. Sharpless and V. V. Fokin, Org.
Lett., 2004, 6, 2853–2855.
5 Striking examples are found in: (a) X. Liu, Y. Liu, G. Li and
R. Warmuth, Angew. Chem., Int. Ed., 2006, 45, 901–904;
(b) Y. Liu, X. Liu and R. Warmuth, Chem.–Eur. J., 2007, 13,
8953–8959; (c) O. Francesconi, A. Ienco, G. Moneti, C. Nativi and
S. Roelens, Angew. Chem., Int. Ed., 2006, 45, 6693–6696;
(d) P. Mal, D. Schultz, K. Beyeh, K. Rissanen and
J. R. Nitschke, Angew. Chem., Int. Ed., 2008, 47, 8297–8301;
(e) K. S. Chichak, S. J. Cantrill, A. R. Pease, S.-H. Chiu, G. W.
V. Cave, J. L. Atwood and J. F. Stoddart, Science, 2004, 304,
1308–1312.
Scheme 4 Proton shifts upon complexation of Zn(II), Dd values in
ppm.
6 (a) J. Gawronski, H. Ko"bon, M. Kwit and A. Katrusiak, J. Org.
Chem., 2000, 65, 5768–5773; (b) M. Chadim, M. Budesınsky,
J. Hodacova, J. Zavada and P. C. Junk, Tetra-
hedron: Asymmetry, 2001, 12, 127–133; (c) N. Kuhnert,
G. M. Rossignolo and A. Lopez-Periago, Org. Biomol. Chem.,
2003, 1, 1157–1170; (d) N. Kuhnert, A. Lopez-Periago and
G. M. Rossignolo, Org. Biomol. Chem., 2005, 3, 524–537;
(e) J. Gawronski, K. Gawronska, J. Grajewski, M. Kwit,
A. Plutecka and U. Rychlewska, Chem.–Eur. J., 2006, 12,
1807–1817.
this entity, we now plan to design related architectures fitted
with chemical moieties able to act as organocatalyst, thus
opening new perspectives for pseudo-enzymatic catalysis.
Currently, the host–guest studies of these new cages with
cations, as well as small organic molecules, are underway in
our laboratory.
7 For reviews on alkyne-azide cycloaddition see: (a) M. Meldal and
C. W. Tornøe, Chem. Rev., 2008, 108, 2952–3015; (b) V. D. Bock,
H. Hiemstra and J. H. van Maarseveen, Eur. J. Org. Chem., 2006,
51–68.
8 For an example of quantification of binding constants by mass-
spectrometry see: M. Desage-El Murr, S. Nowaczyk, T. Le Gall,
C. Mioskowski, B. Amekraz and C. Moulin, Angew. Chem., Int.
Ed., 2003, 42, 1289–1293.
9 For comparison of coordination behaviors of tripodal ligands see:
C.-Y. Su, B.-S. Kang, T.-B. Wen, Y.-X. Tong, X.-P. Yang,
C. Zhang, H.-Q. Liu and J. Sun, Polyhedron, 1999, 18, 1577–1585.
10 For a discussion on the binding of tristriazole ligands with Cu(I)
and (II) see: V. O. Rodionov, S. I. Presolski, D. Diaz Diaz,
V. V. Fokin and M. G. Finn, J. Am. Chem. Soc., 2007, 129,
12705–12712.
Notes and references
1 (a) W. B. Motherwell, M. J. Bingham and Y. Six, Tetrahedron,
2001, 57, 4663–4686; (b) Y. Murakami, J.-I. Kikuchi, Y. Hisaeda
and O. Hayashida, Chem. Rev., 1996, 96, 721–758.
2 (a) X. Zeng, N. Hucher, O. Reinaud and I. Jabin, J. Org. Chem.,
2004, 69, 6886–6889; (b) U. Darbost, M.-N. Rager, S. Petit,
I. Jabin and O. Reinaud, J. Am. Chem. Soc., 2005, 127,
8517–8525; (c) I. Jabin and O. Reinaud, J. Org. Chem., 2003, 68,
3416–3419; (d) O. Seneque, M.-N. Rager, M. Giorgi and
O. Reinaud, J. Am. Chem. Soc., 2000, 122, 6183–6189.
3 For a similar strategy with C2v symmetrical calix[4]pyrroles:
C.-H. Lee, H. Miyaji, D.-W. Yoon and J. L. Sessler, Chem.
Commun., 2008, 24–34.
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