Supramolecular recognition and structural elucidation of inclusion complexes of an achiral carbene precursor in β- and permethylated β-cyclodextrin

Organic Letters

Volumn 6, Issue 12, 2004, Pages 1967-1970

  Mieusset, Jean Luc ^a   Krois, Daniel ^a   Pacar, Mirjana ^a   Brecker, Lothar ^a   Giester, Gerald ^a,b   Brinker, Udo H ^a  

^a INSTITUT FÜR ORGANISCHE CHEMIE   (Austria)

^b UNIVERSITY OF VIENNA   (Austria)

Author keywords

[No Author keywords available]

Indexed keywords

8 AZABICYCLO[3.2.1]OCTAN 3 OL; BETA CYCLODEXTRIN; CARBENE; CYCLODEXTRIN DERIVATIVE; TRI O METHYL BETA CYCLODEXTRIN; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL STRUCTURE; CHIRALITY; CIRCULAR DICHROISM; COMPLEX FORMATION; MOLECULAR RECOGNITION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PHASE TRANSITION; SOLID; STRUCTURE ANALYSIS; SUPRAMOLECULAR CHEMISTRY;

EID: 3042790207     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol049478o     Document Type: Article

References (32)

1. Brinker, U. H.; Rosenberg, M. G. In Advances in Carbene Chemistry; Brinker, U. H., Ed.; JAI: Stamford, CT, 1998; Vol. 2, pp 29-44. McAlpine, S. R.; Garcia-Garibay, M. A. J. Am. Chem. Soc. 1996, 118, 2750. Smith, S. H.; Forrest, S. M.; Williams, D. C.; Acquavella, M. F.; Abelt, C. J. Carbohydr. Res. 1992, 230, 289. Komiyama, M.; Hirai, H. Bull. Chem. Soc. Jpn, 1981, 54, 2053.
2. Brinker, U. H.; Rosenberg, M. G. In Advances in Carbene Chemistry; Brinker, U. H., Ed.; JAI: Stamford, CT, 1998; Vol. 2, pp 29-44. McAlpine, S. R.; Garcia-Garibay, M. A. J. Am. Chem. Soc. 1996, 118, 2750. Smith, S. H.; Forrest, S. M.; Williams, D. C.; Acquavella, M. F.; Abelt, C. J. Carbohydr. Res. 1992, 230, 289. Komiyama, M.; Hirai, H. Bull. Chem. Soc. Jpn, 1981, 54, 2053.
3. Brinker, U. H.; Rosenberg, M. G. In Advances in Carbene Chemistry; Brinker, U. H., Ed.; JAI: Stamford, CT, 1998; Vol. 2, pp 29-44. McAlpine, S. R.; Garcia-Garibay, M. A. J. Am. Chem. Soc. 1996, 118, 2750. Smith, S. H.; Forrest, S. M.; Williams, D. C.; Acquavella, M. F.; Abelt, C. J. Carbohydr. Res. 1992, 230, 289. Komiyama, M.; Hirai, H. Bull. Chem. Soc. Jpn, 1981, 54, 2053.
4. Brinker, U. H.; Rosenberg, M. G. In Advances in Carbene Chemistry; Brinker, U. H., Ed.; JAI: Stamford, CT, 1998; Vol. 2, pp 29-44. McAlpine, S. R.; Garcia-Garibay, M. A. J. Am. Chem. Soc. 1996, 118, 2750. Smith, S. H.; Forrest, S. M.; Williams, D. C.; Acquavella, M. F.; Abelt, C. J. Carbohydr. Res. 1992, 230, 289. Komiyama, M.; Hirai, H. Bull. Chem. Soc. Jpn, 1981, 54, 2053.
5. Fickes, G. N.; Rose, C. B. J. Org. Chem. 1972, 37, 2898.
6. Krois, D.; Bobek, M. M.; Werner, A.; Kählig, H.; Brinker, U. H. Org. Lett. 2000, 2, 315.
7. Schurig, V.; Jung, M.; Schmalzing, D.; Schleimer, M.; Duvekot, J.; Buyten, J. C.; Peene, J. A.; Mussche, P. J. High Resolut. Chromatogr. 1990, 13, 470.
8. Foote, C. S.; Woodward, R. B. Tetrahedron 1964, 20, 687.
9. Povárny, M.; Scheiber, P.; Kraiss, G.; Nádor, K. Tetrahedron. Lett. 1984, 25, 1311.
10. Schmitz, E.; Ohme, R. Chem. Ber. 1961, 94, 2166.
11. Schneider, H.-J.; Hacket, F.; Rüdiger, V.; Ikeda, I. Chem. Rev. 1998, 98, 1755.
12. Job, P. Ann. Chim. 1928, 9, 113. Gil, V. M. S.; Oliveira, N. C. J. Chem. Educ. 1990, 67, 473. Djedaïni, F.; Lin, S. Z.; Perly, B.; Wouessidjewe, D. J. Pharm. Sci. 1990, 79, 643.
13. Job, P. Ann. Chim. 1928, 9, 113. Gil, V. M. S.; Oliveira, N. C. J. Chem. Educ. 1990, 67, 473. Djedaïni, F.; Lin, S. Z.; Perly, B.; Wouessidjewe, D. J. Pharm. Sci. 1990, 79, 643.
14. Job, P. Ann. Chim. 1928, 9, 113. Gil, V. M. S.; Oliveira, N. C. J. Chem. Educ. 1990, 67, 473. Djedaïni, F.; Lin, S. Z.; Perly, B.; Wouessidjewe, D. J. Pharm. Sci. 1990, 79, 643.
15. Fielding, L. Tetrahedron 2000, 56, 6151. Schneider, H.-J.; Yatsimirsky, A. Principles and Methods in Supramolecular Chemistry; Wiley: Chichester, 2000; p 137.
16. Fielding, L. Tetrahedron 2000, 56, 6151. Schneider, H.-J.; Yatsimirsky, A. Principles and Methods in Supramolecular Chemistry; Wiley: Chichester, 2000; p 137.
17. Machuca-Herrera, J. O. J. Chem. Educ. 1997, 74, 448.
18. Zielinski, T. J.; Allendoerfer, R. D. J. Chem. Educ. 1997, 74, 1001. González-Gaitano, G.; Tardajos, G. J. Chem. Educ. 2004, 81, 270.
19. Zielinski, T. J.; Allendoerfer, R. D. J. Chem. Educ. 1997, 74, 1001. González-Gaitano, G.; Tardajos, G. J. Chem. Educ. 2004, 81, 270.
20. Salvatierra, D.; Diez, C.; Jaime, C. J. Inclusion Phenom. 1997, 27, 215.
21. Scatchard, G. Ann. N. Y. Acad. Sci. 1949, 51, 660.
22. Krois, D.; Brinker, U. H. J. Am. Chem. Soc. 1998, 120, 11627.
23. Botsi, A.; Yannakopoulou, K.; Perly, B.; Hadjoudis, E. J. Org. Chem. 1995, 60, 4017.
24. Neuhaus, D.; Keeler, J. J. Magn. Reson. 1986, 68, 568.
25. Zubiaur, M.; Jaime, C. J. Org. Chem. 2000, 65, 8139.
26. Bobek, M. M.; Giester, G.; Kählig, H.; Brinker, U. H. Tetrahedron Lett. 2000, 41, 5663.
27. Cardinael, P.; Peulon, V.; Perez, G.; Coquerel, G.; Toupet, L. J. Inclusion Phenom. 2001, 39, 159.
28. Caira, M. R.; Griffith, V. J.; Nassimbeni, L. R.; Van Outdshoorn, B. Supramol. Chem. 1996, 7, 119.
29. Rontoyianni, A.; Mavridis, I. M.; Israel, R.; Beurskens, G. J. Inclusion Phenom. 1998, 32, 415.
30. Immel, S.; Lichtenthaler, F. W. Starch 1996, 48, 225.
31. Grandeury, A.; Petit, S.; Gouhier, G.; Agasse, V.; Coquerel, G. Tetrahedron: Asymmetry 2003, 14, 2143.
32. Makedonopoulou, S.; Yannakopoulou, K.; Mentzafos, D.; Lamzin, V.; Popov, A.; Mavridis, I. M. Acta Crystallogr. 2001, B57, 399.