Cucurbituril-mediated supramolecular acid catalysis

Organic Letters

Volumn 11, Issue 12, 2009, Pages 2595-2598

  Klöck, Cornelius ^a   Dsouza, Roy N ^a   Nau, Werner M ^a  

^a JACOBS UNIVERSITY BREMEN   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

BRIDGED COMPOUND; CADAVERINE; CUCURBIT(6)URIL; CUCURBIT(7)URIL; CUCURBITURIL; IMIDAZOLE DERIVATIVE; MACROCYCLIC COMPOUND;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; HYDROLYSIS;

BRIDGED COMPOUNDS; CADAVERINE; CATALYSIS; HYDROLYSIS; IMIDAZOLES; MACROCYCLIC COMPOUNDS; MOLECULAR STRUCTURE;

EID: 67149115142     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol900920p     Document Type: Article

References (43)

1. Artificial Enzymes; Breslow, R., Ed.; Wiley-VCH: Weinheim, 2005.
2. Cramer, F. Angew. Chem. 1961, 73, 49-56.
3. Tabushi, I. Acc. Chem. Res. 1982, 15, 66-72.
4. Anslyn, E.; Breslow, R. J. Am. Chem. Soc. 1989, 111, 5972-5973.
5. Breslow, R.; Zhang, B. L. J. Am. Chem. Soc. 1992, 114, 5882-5883.
6. Breslow, R.; Dong, S. D. Chem. Rev. 1998, 98, 1997-2012.
7. Chen, J.; Korner, S.; Craig, S. L.; Rudkevich, D. M.; Rebek, J. Nature 2002, 415, 385-386.
8. Westheimer, F. H. Tetrahedron 1995, 51, 3-20.
9. Pluth, M. D.; Bergman, R. G.; Raymond, K. N. Science 2007, 316, 85-88.
10. Pluth, M. D.; Bergman, R. G.; Raymond, K. N. J. Am. Chem. Soc. 2008, 130, 11423-11429.
11. Pluth, M. D.; Bergman, R. G.; Raymond, K. N. J. Am. Chem. Soc. 2007, 129, 11459-11467.
12. Bakirci, H.; Koner, A. L.; Schwarzlose, T.; Nau, W. M. Chem.-Eur. J. 2006, 12, 4799-4807.
13. Marquez, C.; Nau, W. M. Angew. Chem., Int. Ed. 2001, 40, 3155-3160.
14. Saleh, N.; Koner, A. L.; Nau, W. M. Angew. Chem., Int. Ed. 2008, 47, 5398-5401.
15. Wang, R.; Macartney, D. H. Org. Biomol. Chem. 2008, 6, 1955-1960.
16. Abraham, W. J. Incl. Phenom. Macrocycl. Chem. 2002, 43, 159-174.
17. Guo, D.-S.; Wang, K.; Liu, Y. J. Incl. Phenom. Macrocycl. Chem. 2008, 62, 1-21.
18. Lagona, J.; Mukhopadhvay, P.; Chakrabarti, S.; Isaacs, L. Angew. Chem., Int. Ed. 2005, 44, 4844-4870.
19. Rekharsky, M. V.; Inoue, Y. Chem. Rev. 1998, 98, 1875-1917.
20. Vicens, J.; Böhmer, V. Calixarenes: A Versatile Class of Macro-cyclic Compounds: Kluwer Academic Publishers: Dordrecht, 1991.
21. Liu, S.; Ruspic, C.; Mukhopadhyay, P.; Chakrabarti, S.; Zavalij, P. Y.; Isaacs, L. J. Am. Chem. Soc. 2005, 127, 15959-15967.
22. Mock, W. L.; Irra, T. A.; Wepsiec, J. P.; Manimaran, T. L. J. Org. Chem. 1983, 48, 3619-3620.
23. Mock, W. L.; Trra, T. A.; Wepsiec, J. P.; Adhya, M. J. Org. Chem. 1989, 54, 5302-5308.
24. Krasia, T. C.; Steinke, J. H. G. J. Chem. Commun. 2002, 22-23.
25. Jon, S. Y.; Ko, Y. H.; Park, S. H.; Kim, H.-J.; Kim, K. Chem. Commun. 2001, 1938-1939.
26. Maddipatla, M. V. S. N.; Kaanumalle, L. S.; Natarajan, A.; Pattabiraman, M.; Ramamurthy, V. Langmuir 2007, 23, 7545-7554.
27. Pattabiraman, M.; Natarajan, A.; Kaanumalle, L. S.; Ramamurthy, V. Org. Lett. 2005, 7, 529-532.
28. Wang, R.; Yuan, L.; Macartney, D. H. J. Org. Chem. 2006, 71, 1237-1239.
29. Mock, W. L.; Shih, N. Y. J. Org. Chem. 1983, 48, 3618-3619.
30. O'Connor, C. O. Rev. Chem. Soc. 1970, 24, 553-564.
31. Armstrong, V. C.; Farlow, D. W.; Moodie, R. B. J. Chem. Soc. B 1968, 1099-1103.
32. Zahn, D. Eur. J. Org. Chem. 2004, 4020-4023.
33. Hennig, A.; Bakirci, H.; Nau, W. M. Nat. Methods 2007, 4, 629-632.
34. The product of the reaction (cadaverine) is doubly positively charged under the reaction conditions and was therefore expected to bind more strongly to cucurbiturils than the singly positively charged reactants 1 and 2. Deviations from first order kinetics were therefore expected at high conversion.
35. Laidler, K. J. Pure Appl. Chem. 1996, 68, 149-192.
36. Buschmann, H.-J.; Cleve, E.; Schollmeyer, E. Inorg. Chim. Acta 1992, 193, 93-97.
37. Hwang, I.; Jeon, W. S.; Kim, H.-J.; Kim, D.; Kim, H.; Selvapalam, N.; Eujita, N.; Shinkai, S.; Kim, K. Angew. Client., Int. Ed. 2007, 46, 210-213.
38. Armstrong, V. C.; Moodie, R. B. J. Chem. Soc. B 1969, 934-939.
39. Lee, I.; Kim, C. K.; Lee, B. C. J. Comput. Chem. 1987, 8, 794-800,
40. Calzadilla, M.; Malpica, A.; Cordova, T. J. Phys. Org. Chem. 1999, 12, 708-712.
41. Malpica, A.; Calzadilla, M.; Baumrueker, J.; Jimenez, J.; Lopez, L.; Escobar, G.; Monies, C. J. Org. Chem. 1994, 59, 3398-3401.
42. Wothers, P.; Greeves, N.; Wanen, S.; Clayden, J. Organic Chemistry; Oxford University Press: New York, 2005.
43. Depuy, C. H.; Ponder, B. W. J. Am. Chem. Soc. 1959, 81, 4629-4631.