First enantiopure calix[6]aza-cryptand: Synthesis and chiral recognition properties towards neutral molecules

Tetrahedron Asymmetry

Volumn 16, Issue 23, 2005, Pages 3767-3771

  Garrier, Eva ^a   Gac, Stéphane Le ^a   Jabin, Ivan ^a  

^a UNIVERSITÉ DU HAVRE   (France)

Author keywords

[No Author keywords available]

Indexed keywords

CALIXARENE; HETEROCYCLIC COMPOUND; PROTON;

ARTICLE; CHEMISTRY; CHIRALITY; CONFORMATION; ENANTIOMER; ENANTIOSELECTIVITY; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; PROTON TRANSPORT; SYNTHESIS;

EID: 28644444132     PISSN: 09574166     EISSN: 1362511X     Source Type: Journal    
DOI: 10.1016/j.tetasy.2005.10.039     Document Type: Article

References (50)

1. T.H. Webb, and C.S. Wilcox Chem. Soc. Rev. 1993 383 395
2. B. Chankvetadze, G. Endresz, and G. Blaschke Chem. Soc. Rev. 1996 141 153
3. L. Pu Chem. Rev. 104 2004 1687 1716
4. C.J. Easton, and S.F. Lincoln Chem. Soc. Rev. 1996 163 170
5. M.V. Rekharsky, and Y. Inoue J. Am. Chem. Soc. 124 2002 813 826
6. A. Grandeury, S. Petit, G. Gouhier, V. Agasse, and G. Coquerel Tetrahedron: Asymmetry 14 2003 2143 2152
7. Leading examples of chiral recognition inside a cavity of enantiopure organic macrocycles: J. Costante-Crassous, T.J. Marrone, J.M. Briggs, J.A. McCammon, and A. Collet J. Am. Chem. Soc. 119 1997 3818 3823
8. J. Yoon, and D.J. Cram J. Am. Chem. Soc. 119 1997 11796 11806
9. J.M. Rivera, T. Martin, and J. Rebek Jr. J. Am. Chem. Soc. 123 2001 5213 5220
10. B. Botta, M. Botta, A. Filippi, A. Tafi, G. Delle Monache, and M. Speranza J. Am. Chem. Soc. 124 2002 7658 7659
11. For general references on calixarenes, see: C.D. Gutsche J.F. Stoddart Calixarenes Revisited, Monographs in Supramolecular Chemistry 1998 The Royal Society of Chemistry Cambridge, UK
12. L. Mandolini R. Ungaro Calixarenes in Action 2000 Imperial College Press London
13. The cavity of the more studied calix[4]arenes is not well adapted for the inclusion of organic molecules. Thus, they have mainly been used for the preorganization of a chiral binding site outside of the cavity. For recent leading references on chiral recognition with calix[4]arenes, see: C. Lynam, K. Jennings, K. Nolan, P. Kane, M. Anthony McKervey, and D. Diamond Anal. Chem. 74 2002 59 66
14. Y. He, Y. Xiao, L. Meng, Z. Zeng, X. Wu, and C.-T. Wu Tetrahedron Lett. 43 2002 6249 6253
15. W. Guo, J. Wang, C. Wang, J.-Q. He, X.-W. He, and J.-P. Cheng Tetrahedron Lett. 43 2002 5665 5667
16. I. Bitter, E. Koszegi, A. Grun, P. Bako, K. Pal, A. Grofcsik, M. Kubinyi, B. Balazs, and G. Toth Tetrahedron: Asymmetry 14 2003 1025 1035
17. Y.-S. Zheng, and C. Zhang Org. Lett. 6 2004 1189 1192
18. C. Gaeta, M. De Rosa, M. Fruilo, A. Soriente, and P. Neri Tetrahedron: Asymmetry 16 2005 2333 2340
19. J. Luo, Q.-Y. Zheng, C.-F. Chen, and Z.-T. Huang Tetrahedron 61 2005 8517 8528
20. T. Arimura, H. Kawabata, T. Matsuda, T. Muramatsu, H. Satoh, K. Fujio, O. Manabe, and S. Shinkai J. Org. Chem. 56 1991 301 306
21. T. Grady, S.J. Harris, M.R. Smyth, D. Diamond, and P. Hailey Anal. Chem. 68 1996 3775 3782
22. A. Soi, J. Pfeiffer, J. Jauch, and V. Schurig Tetrahedron: Asymmetry 10 1999 177 182
23. H.-S. Yuan, Y. Zhang, Y.-J. Hou, X.-Y. Zhang, X.-Z. Yang, and Z.-T. Huang Tetrahedron 56 2000 9611 9617
24. See also for a review on chiral calixarenes: M. Vysotsky, C. Schmidt, and V. Böhmer Advances in Supramolecular Chemistry Vol. 7 2000 JAI Press 139 233
25. U. Lüning, F. Löffler, and J. Eggert Z. Asfari Calixarenes 2001 2001 Kluwer Academic Publishers Dordrecht, The Netherlands
26. O. Sénèque, M.-N. Rager, M. Giorgi, and O. Reinaud J. Am. Chem. Soc. 122 2000 6183 6189
27. Y. Rondelez, M.-N. Rager, A. Duprat, and O. Reinaud J. Am. Chem. Soc. 124 2002 1334 1340
28. A.M. Rincon, P. Prados, and J. de Mendoza Eur. J. Org. Chem. 2002 640 644
29. I. Jabin, and O. Reinaud J. Org. Chem. 68 2003 3416 3419
30. U. Darbost, M. Giorgi, O. Reinaud, and I. Jabin J. Org. Chem. 69 2004 4879 4884
31. X. Zeng, N. Hucher, O. Reinaud, and I. Jabin J. Org. Chem. 69 2004 6886 6889
32. U. Darbost, X. Zeng, M.-N. Rager, M. Giorgi, I. Jabin, and O. Reinaud Eur. J. Inorg. Chem. 2004 4371 4374
33. G. Izzet, B. Douziech, T. Prangé, A. Tomas, I. Jabin, Y. Le Mest, and O. Reinaud Proc. Natl. Acad. Sci. 102 2005 6831 6836
34. See also: K. Kim, H.J. Lee, and J.-I. Choe Bull. Korean Chem. Soc. 26 2005 645 651
35. U. Darbost, M.-N. Rager, S. Petit, I. Jabin, and O. Reinaud J. Am. Chem. Soc. 127 2005 8517 8525
36. U. Darbost, M. Giorgi, N. Hucher, I. Jabin, and O. Reinaud Supramol. Chem. 17 2005 243 250
37. R.G. Janssen, W. Verboom, D.N. Reinhoudt, A. Casnati, M. Freriks, A. Pochini, F. Uggozoli, R. Ungaro, P.M. Nieto, M. Carramolino, F. Cuevas, P. Prados, and J. de Mendoza Synthesis 1993 380 385
38. See Ref. 11a.
39. J. Farràs, X. Ginesta, P.W. Sutton, J. Taltavull, F. Egeler, P. Romea, F. Urpi, and J. Vilarrasa Tetrahedron 57 2001 7665 7674
40. 3) δ 17.15, 37.00, 38.86, 124.5, 131.3, 132.4, 132.7, 134.5.
41. J.M. Siaugue, F. Segat-Dioury, I. Sylvestre, A. Favre-Réguillon, J. Foos, C. Madic, and A. Guy Tetrahedron 57 2001 4713 4718
42. 3) δ 19.26, 41.38, 49.40, 54.42, 61.22, 125.3(6), 125.4(3), 130.9, 133.0(8), 133.1(2), 133.3, 133.8(0), 133.8(6), 133.9(3), 147.7, 148.0.
43. 3/calix ratio: S. Le Gac, X. Zeng, O. Reinaud, and I. Jabin J. Org. Chem. 70 2005 1204 1210
44. 2 = 5 Hz, 1H), 8.35 (d, J = 8 Hz, 1H), 8.46 (d, J = 8 Hz, 1H).
45. 3) δ 1.01-1.11 (m, 39H), 1.15 (s, 9H), 1.18 (s, 9H), 2.29 (d, J = 11 Hz, 1H), 2.36-2.48 (m, 2H), 2.52 (d, J = 12 Hz, 1H), 2.66-3.19 (m, 13H), 2.83 (s, 3H), 3.00 (s, 3H), 3.06 (s, 3H), 3.31-3.53 (m, 6H), 3.78-4.19 (m, 6H), 4.41-4.62 (m, 6H), 6.91-7.13 (m, 12H).
46. 1H NMR signals were attributed through 2D NMR experiments (COSY, HMQC).
47. 3).
48. T], was found to be at least 1360 (errors estimated ±10%).
49. For the preparation of this compound, see: S. Cortes, and H. Kohn J. Org. Chem. 48 1983 2246 2254
50. Recently the selective endo-complexation of l- or d-leucine has been described in the solid state but with an achiral calix[6]arene, see J.L. Atwood, S.J. Dalgarno, M.J. Hardie, and C.L. Raston Chem. Commun. 2005 337 339