Enantioselective catalysis of the aza-cope rearrangement by a chiral supramolecular assembly

Journal of the American Chemical Society

Volumn 131, Issue 48, 2009, Pages 17530-17531

  Brown, Casey J ^a   Bergman, Robert G ^a   Raymond, Kenneth N ^a  

^a NONE

Author keywords

[No Author keywords available]

Indexed keywords

AZA-COPE REARRANGEMENT; CHIRAL CAVITY; ENANTIOMERIC EXCESS; ENANTIOPURE; ENANTIOSELECTIVE CATALYSIS; REACTIVE CONFORMATION; SUPRAMOLECULAR ASSEMBLIES; SUPRAMOLECULAR CATALYSTS;

CATALYSIS; ELECTRON TRANSITIONS; ENANTIOSELECTIVITY; GALLIUM; NAPHTHALENE;

SUPRAMOLECULAR CHEMISTRY;

CATION; ENAMMONIUM CATION; HETEROCYCLIC COMPOUND; SELF ASSEMBLED MONOLAYER; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHIRALITY; CONFORMATION; ENANTIOMER; ENANTIOSELECTIVITY; ENZYME SUBSTRATE; SUPRAMOLECULAR CHEMISTRY;

EID: 72249089328     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja906386w     Document Type: Article

References (28)

1. (a) Iwasawa, T.; Hooley, R. J.; Rebek, J. Science 2007, 317, 493.
2. (b) Dong, V. M.; Fiedler, D.; Carl, B.; Bergman, R. G.; Raymond, K. N. J. Am. Chem. Soc. 2006, 128, 14464.
3. (c) Brumaghim, J. L.; Michels, M.; Raymond, K. N. Eur. J. Org. Chem. 2004, 4552.
4. (d) Kuil, M.; Soltner, T.; Van Leeuwen, P. W. N. M; Reek, J. N. H. J. Am. Chem. Soc. 2006, 128, 11344.
5. (a) Yoshizawa, M.; Tamura, M.; Fujita, M. Science 2006, 312, 251.
6. (b) Pluth, M. D.; Bergman, R. G.; Raymond, K. N. Science 2007, 316, 85.
7. (c) Hou, J. L.; Ajami, D.; Rebek, J. J. Am. Chem. Soc. 2008, 130, 7810.
8. (a) Leung, D. H.; Bergman, R. G.; Raymond, K. N. J. Am. Chem. Soc. 2007, 129, 2746.
9. (b) Leung, D. H.; Bergman, R. G.; Raymond, K. N. J. Am. Chem. Soc. 2006, 128, 9781.
10. (c) Seneque, O.; Rager, M. N.; Giorgi, M.; Reinaud, O. J. Am. Chem. Soc. 2000, 122, 6183.
11. (d) Natarajan, A.; Kaanumalle, L. S.; Jockusch, S.; Gibb, C. L. D.; Gibb, B. C.; Turro, N. J.; Ramamurthy, V. J. Am. Chem. Soc. 2007, 129, 4132.
12. (a) Hembury, G. A.; Borovkov, V. V.; Inoue, Y. Chem. Rev. 2008, 108, 1.
13. (b) Koblenz, T. S.; Wassenaar, J.; Reek, J. N. H. Chem. Soc. Rev. 2008, 37, 247.
14. (a) Lu, R.; Yang, C.; Cao, Y.; Tong, L.; Jiao, W.; Wada, T.; Wang, Z.; Mori, T.; Inoue, Y. J. Org. Chem. 2008, 73, 7695.
15. (b) Nishioka, Y.; Yamaguchi, T.; Kawano, M.; Fujita, M. J. Am. Chem. Soc. 2008, 130, 8160.
16. (c) Lee, S. J.; Cho, S.-H.; Mulfort, K. L.; Tiede, D. M.; Hupp, J. T.; Nguyen, S. T. J. Am. Chem. Soc. 2008, 130, 16828.
17. (d) Yang, C.; Mori, T.; Inoue, Y. J. Org. Chem. 2008, 73, 5876.
18. (e) Yang, C.; Mori, T.; Origane, Y.; Ko, Y. H.; Selvapalam, N.; Kim, K.; Inoue, Y. J. Am. Chem. Soc. 2008, 130, 8574.
19. Caulder, D.; Raymond, K. N. J. Chem. Soc., Dalton Trans. 1999, 1185.
20. Pluth, M. D.; Bergman, R. G.; Raymond, K. N. Angew. Chem., Int. Ed. 2007, 46, 8587.
21. (b) Pluth, M. D.; Bergman, R. G.; Raymond, K. N. J. Am. Chem. Soc. 2008, 130, 11423.
22. (c) Fiedler, D.; van Halbeek, H.; Bergman, R. G.; Raymond, K. N. J. Am. Chem. Soc. 2006, 128, 10240.
23. (d) Hastings, C. J.; Fiedler, D.; Bergman, R. G.; Raymond, K. N. J. Am. Chem. Soc. 2008, 130, 10977.
24. Ziegler, M.; Davis, A. V.; Johnson, D. W.; Raymond, K. N. Angew. Chem., Int. Ed. 2003, 42, 665.
25. Davis, A. V.; Fiedler, D.; Ziegler, M.; Terpin, A.; Raymond, K. N. J. Am. Chem. Soc. 2007, 129, 15354.
26. High shape specificity in chiral recognition by 1 has also been observed in the C-H activation of aldehydes by prochiral iridium half-sandwich complexes (see ref 5a), but the earlier system was not catalytic and was not designed to allow isolation of enantioenriched product.
27. 6 is used.
28. Hiersemann, M.; Abraham, L. Eur. J. Org. Chem. 2002, 1461.