Enzymelike catalysis of the nazarov cyclization by supramolecular encapsulation

Journal of the American Chemical Society

Volumn 132, Issue 20, 2010, Pages 6938-6940

  Hastings, Courtney J ^a,b   Pluth, Michael D ^a,b   Bergman, Robert G ^a,b   Raymond, Kenneth N ^a,b  

^a UNIVERSITY OF CALIFORNIA   (United States)

^b LAWRENCE BERKELEY NATIONAL LABORATORY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AQUEOUS CONDITION; CATALYZED REACTIONS; ENZYMATIC SYSTEM; MILD TEMPERATURES; NAZAROV CYCLIZATION; PROTONATED; RATE ENHANCEMENT; SELF-ASSEMBLED; TETRAHEDRAL ASSEMBLY;

CATALYSIS; CYCLIZATION; GALLIUM;

REACTION INTERMEDIATES;

AMMONIA; CARBON; ENZYME; NAPHTHALENE; PHOSPHONIUM DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL BOND; CHEMICAL REACTION; CYCLIZATION; ENCAPSULATION; PROTON TRANSPORT; STOICHIOMETRY; SUPRAMOLECULAR CHEMISTRY;

ALCOHOLS; BIOMIMETICS; CARBON; CATALYSIS; CYCLIZATION; ENZYMES; KINETICS; LIGANDS; MODELS, MOLECULAR; MOLECULAR CONFORMATION; TEMPERATURE;

EID: 77952571387     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja102633e     Document Type: Article

References (30)

1. Cram, D. J. Angew. Chem., Int. Ed. Engl. 1988, 27, 1009
2. Hof, F., Craig, S. L., Nuckolls, C., and Rebek, J. Angew. Chem., Int. Ed. 2002, 41, 1488
3. Oshovsky, G. V., Reinhoudt, I. D. N., and Verboom, W. Angew. Chem., Int. Ed. 2007, 46, 2366
4. Schmuck, C. Angew. Chem., Int. Ed. 2007, 46, 5830
5. Steed, J. W. and Atwood, J. L. Supramolecular Chemistry, 1 st ed.; Wiley: Chichester, U.K., 2000.
6. Breslow, R. and Dong, S. D. Chem. Rev. 1998, 98, 1997
7. Kirby, A. J. Angew. Chem., Int. Ed. Engl. 1996, 35, 708
8. Vriezema, D. M., Aragonès, M. C., Elemans, J. A. A. W., Cornelissen, J. J. L. M., Rowan, A. E., and Nolte, R. J. M. Chem. Rev. 2005, 105, 1445
9. Yoshizawa, M., Klosterman, J. K., and Fujita, M. Angew. Chem., Int. Ed. 2009, 48, 3418
10. Jencks, W. P. Catalysis in Chemistry and Enzymology; McGraw-Hill: New York, 1969.
11. Radzicka, A. and Wolfenden, R. A. Science 1995, 267, 90
12. Caulder, D. L. and Raymond, K. N. Acc. Chem. Res. 1999, 32, 975
13. Work by other groups on metal-ligand polyhedra is described in the following articles and the references therein: Fujita, M., Tominaga, M., Hori, A., and Therrien, B. Acc. Chem. Res. 2005, 38, 369
14. Northrop, B. H., Zheng, Y., Chi, K., and Stang, P. J. Acc. Chem. Res. 2009, 42, 1554
15. Saalfrank, R. W., Maid, H., and Scheurer, A. Angew. Chem., Int. Ed. 2008, 47, 8794
16. Biros, S. M., Bergman, R. G., and Raymond, K. N. J. Am. Chem. Soc. 2007, 129, 12094
17. Pluth, M. D., Bergman, R. G., and Raymond, K. N. J. Am. Chem. Soc. 2007, 129, 11459
18. Pluth, M. D., Bergman, R. G., and Raymond, K. N. Acc. Chem. Res. 2009, 42, 1650 and references therein
19. Fiedler, D., van Halbeek, H., Bergman, R. G., and Raymond, K. N. J. Am. Chem. Soc. 2006, 128, 10240
20. Campbell, P. H., Chiu, N. W. K., Deugau, K., Miller, I. J., and Sorensen, T. S. J. Am. Chem. Soc. 1969, 91, 6404
21. Threlkel, R. S., Bercaw, J. E., Seidler, P. F., Stryker, J. M., and Bergman, R. G. Organic Syntheses; Wiley: New York, 1993; Collect. Vol. VIII, pp 505 - 508.
22. King, R. B. and Bisnette, M. B. J. Organomet. Chem. 1967, 8, 287
23. Hastings, C. J., Fiedler, D., Bergman, R. G., and Raymond, K. N. J. Am. Chem. Soc. 2008, 130, 10977
24. Kang, J. M., Hilmersson, G., Santamaria, J., and Rebek, J. J. Am. Chem. Soc. 1998, 120, 3650
25. Nishioka, Y., Yamaguchi, T., Yoshizawa, M., and Fujita, M. J. Am. Chem. Soc. 2007, 129, 7000
26. Yoshizawa, M., Takeyama, Y., Kusukawa, T., and Fujita, M. Angew. Chem., Int. Ed. 2002, 41, 1347
27. 2O of Cp*H relative to 2 resulting from the greater solubility of 2 in water.
28. Mock, W. L., Irra, T. A., Wepsiec, J. P., and Adhya, M. J. Org. Chem. 1989, 54, 5302
29. Marinescu, L. G. and Bols, M. Angew. Chem., Int. Ed. 2006, 45, 4590 Very large rate accelerations were observed in the stoichiometric acylation of cyclodextrins: Trainor, G. L. and Breslow, R. J. Am. Chem. Soc. 1981, 103, 154 Million-fold rate enhancements were observed using an enzyme-mimicking polymer catalyst: Skouta, R., Wei, S., and Breslow, R. J. Am. Chem. Soc. 2009, 131, 15604
30. Sorensen, T. S. J. Am. Chem. Soc. 1967, 89, 3782