Aza cope rearrangement of propargyl enammonium cations catalyzed by a self-assembled "nanozyme"

Journal of the American Chemical Society

Volumn 130, Issue 33, 2008, Pages 10977-10983

  Hastings, Courtney J ^a   Fiedler, Dorothea ^a   Bergman, Robert G ^a   Raymond, Kenneth N ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AZA-COPE REARRANGEMENT; PROPARGYL; SELF-ASSEMBLED;

GALLIUM;

AMMONIUM DERIVATIVE; CATION;

ARTICLE; CHEMICAL REACTION; COMPETITIVE INHIBITION; ENTROPY; ENZYME KINETICS; HYDROLYSIS; MICHAELIS MENTEN KINETICS; NANOENCAPSULATION; REACTION ANALYSIS; TURNOVER TIME;

1-NAPHTHYLAMINE; ALKYNES; AZA COMPOUNDS; CATALYSIS; CATIONS; ENTROPY; GALLIUM; KINETICS; LIGANDS; MACROMOLECULAR SUBSTANCES; MODELS, MOLECULAR; MOLECULAR STRUCTURE; ORGANOMETALLIC COMPOUNDS; QUATERNARY AMMONIUM COMPOUNDS; TIME FACTORS;

EID: 50249180231     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja8013055     Document Type: Article

References (50)

1. Jencks, W. P. Catalysis in Chemistry and Enzymology; McGraw-Hill: New York, 1969.
2. Kirby, A. J. Angew. Chem., Int. Ed. Engl. 1996, 35, 707-724.
3. Tramontano, A.; Janda, K. D.; Lerner, R. A. Science 1986, 234, 1566-1570.
4. Borman, S. Chem. Eng. News 2004, 82, 35-39.
5. Hof, F.; Craig, S. L.; Nuckolls, C.; Rebek, J. Angew. Chem., Int. Ed. 2002, 41, 1488-1508.
6. Kleij, A. W.; Reek, J. N. H. Chem. - Eur. J. 2006, 12, 4218-4227.
7. Koblenz, T. S.; Wassenaar, J.; Reek, J. N. H. Chem. Soc. Rev. 2008, 37, 247-262.
8. Lützen, A. Angew. Chem., Int. Ed. 2005, 44, 1000-1002.
9. Motherwell, W. B.; Bingham, M. J.; Six, Y. Tetrahedron 2001, 57, 4663-4686.
10. Oshovsky, G. V.; Reinhoudt, D. N.; Verboom, W. Angew. Chem., Int. Ed. 2007, 46, 2366-2393.
11. Sanders, J. K. M. Chem. - Eur. J. 1998, 4, 1378-1383.
12. Schmuck, C. Angew. Chem., Int. Ed. 2007, 46, 5830-5833.
13. Vriezema, D. M.; Aragonès, M. C.; Elemans, J. A. A. W.; Cornelissen, J. J. L. M.; Rowan, A. E.; Nolte, R. J. M. Chem. Rev. 2005, 105, 1445-1489.
14. Breslow, R.; Dong, S. D. Chem. Rev. 1998, 98, 1997-2012.
15. Cram, D. J. Angew. Chem., Int. Ed. Engl. 1988, 27, 1009-1020.
16. Lehn, J.-M. Angew. Chem., Int. Ed. Engl. 1988, 27, 89-112.
17. Yeh, R. M.; Davis, A. V.; Raymond, K. N. Supramolecular Systems: Self-Assembly. In Comprehensive Coordination Chemistry II; McCleverty, J. A., Meyer, T. J. Eds. Elsevier: Oxford, U.K., 2004; pp 327-355.
18. Mimassi, L.; Guyard-Duhayon, C.; Rager, M. N.; Amouri, H. Inorg. Chem. 2004, 43, 6644-6649.
19. Caulder, D. L.; Bruckner, C.; Powers, R. E.; Konig, S.; Parac, T. N.; Leary, J. A.; Raymond, K. N. J. Am. Chem. Soc. 2001, 123, 8923-8938.
20. Caulder, D. L.; Powers, R. E.; Parac, T. N.; Raymond, K. N. Angew. Chem., Int. Ed. 1998, 37, 1840-1843.
21. Caulder, D. L.; Raymond, K. N. J. Chem. Soc., Dalton Trans. 1999, 1185-1200.
22. Caulder, D. L.; Raymond, K. N. Acc. Chem. Res. 1999, 32, 975-982.
23. Terpin, A. J.; Ziegler, M.; Johnson, D. W.; Raymond, K. N. Angew. Chem., Int. Ed. 2001, 40, 157-160.
24. Ziegler, M.; Davis, A. V.; Johnson, D. W.; Raymond, K. N. Angew. Chem., Int. Ed. 2003, 42, 665-668.
25. Biros, S. M.; Bergman, R. G.; Raymond, K. N. J. Am. Chem. Soc. 2007, 129, 12094-12095.
26. Dong, V. M.; Fiedler, D.; Carl, B.; Bergman, R. G.; Raymond, K. N. J. Am. Chem. Soc. 2006, 128, 14464-14465.
27. Fiedler, D.; Pagliero, D.; Brumaghim, J. L.; Bergman, R. G.; Raymond, K. N. Inorg. Chem. 2004, 43, 846-848.
28. Ziegler, M.; Brumaghim, J. L.; Raymond, K. N. Angew. Chem., Int. Ed. 2000, 39, 4119-4121.
29. Pluth, M. D.; Bergman, R. G.; Raymond, K. N. Science 2007, 316, 85.
30. Leung, D. H.; Bergman, R. G.; Raymond, K. N. J. Am. Chem. Soc. 2006, 128, 9781-9797.
31. Leung, D. H.; Bergman, R. G.; Raymond, K. N. J. Am. Chem. Soc. 2007, 129, 2746-2747.
32. Leung, D. H.; Fiedler, D.; Bergman, R. G.; Raymond, K. N. Angew. Chem., Int. Ed. 2004, 43, 963-966.
33. Kang, J. M.; Hilmersson, G.; Santamaria, J.; Rebek, J. J. Am. Chem. Soc. 1998, 120, 3650-3656.
34. Kang, J. M.; Rebek, J. Nature 1997, 385, 50-52.
35. Kang, J. M.; Santamaria, J.; Hilmersson, G.; Rebek, J. J. Am. Chem. Soc. 1998, 120, 7389-7390.
36. Nishioka, Y.; Yamaguchi, T.; Yoshizawa, M.; Fujita, M. J. Am. Chem. Soc. 2007, 129, 7000-7001.
37. Yoshizawa, M.; Tamaru, M.; Fujita, M. Science 2006, 312, 251-254.
38. Fiedler, D.; Bergman, R. G.; Raymond, K. N. Angew. Chem., Int. Ed. 2004, 43, 6748-6751.
39. Fiedler, D.; van Halbeek, H.; Bergman, R. G.; Raymond, K. N. J. Am. Chem. Soc. 2006, 128, 10240-10252.
40. Elkik, E.; Francesch, C. Bull. Soc. Chim. Fr. 1968, 3, 903-910.
41. Opitz, G. Justus Liebigs Ann. Chem. 1961, 122-132.
42. McKee, T.; McKee, J. R. Biochemistry: The Molecular Basis of Life, 3rd ed.; McGraw-Hill: New York, 2003.
43. Eadie, G. S. J. Biol. Chem. 1942, 146, 85-93.
44. Hofstee, B. H. J. Science 1952, 116, 329-331.
45. Viola, A.; MacMillan, J. H. J. Am. Chem. Soc. 1970, 92, 2404-2410.
46. Gottlieb, H. E.; Kotlyar, V.; Nudelman, A. J. Org. Chem. 1997, 62, 7512-7515.
47. Alaimo, P. J.; Peters, D. W.; Arnold, J.; Bergman, R. G. J. Chem. Educ. 2001, 78, 64.
48. Ellenberger, M. R.; Dixon, D. A.; Farneth, W. E. J. Am. Chem. Soc. 1981, 103, 5377-5382.
49. Corey, E. J.; Fuchs, P. L. Tetrahedron Lett. 1972, 13, 3769-3772.
50. Capon, R. J.; Barrow, R. A. J. Org. Chem. 1998, 63, 75-83.