Selectivity in an encapsulated cycloaddition reaction

Organic Letters

Volumn 4, Issue 3, 2002, Pages 327-329

  Chen, Jian ^a   Rebek Jr , Julius ^a  

^a SCRIPPS RESEARCH INSTITUTE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ARTICLE; CHEMICAL STRUCTURE; INORGANIC CHEMISTRY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY;

CHEMISTRY, INORGANIC; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR STRUCTURE;

EID: 0037034360     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0168115     Document Type: Article

References (17)

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9. Kirmse, W.; Homer, L. Liebigs Ann. 1958, 674, 1. For discussions, see the following: Fleming, I. Frontier Orbitals and Organic Chemical Reactions; Wiley: New York, 1977; p 155. Kolb, H. C.; Finn, M. G.; Sharpless; K. B. Angew. Chem., Int. Ed. 2001, 40, 2004-2021.
10. Kirmse, W.; Homer, L. Liebigs Ann. 1958, 674, 1. For discussions, see the following: Fleming, I. Frontier Orbitals and Organic Chemical Reactions; Wiley: New York, 1977; p 155. Kolb, H. C.; Finn, M. G.; Sharpless; K. B. Angew. Chem., Int. Ed. 2001, 40, 2004-2021.
11. Kirmse, W.; Homer, L. Liebigs Ann. 1958, 674, 1. For discussions, see the following: Fleming, I. Frontier Orbitals and Organic Chemical Reactions; Wiley: New York, 1977; p 155. Kolb, H. C.; Finn, M. G.; Sharpless; K. B. Angew. Chem., Int. Ed. 2001, 40, 2004-2021.
12. Because both reactants form symmetrical complexes (e.g., 9 and 10) the system shows substrate inhibition and does not obey Michaelis-Menten kinetics; for a discussion, see: Fersht, A. Enzyme Structure and Mechanism, 2nd ed.; W. H. Freeman: New York, 1985; p 114.
13. For a discussion, see: Nakash, M.; Clyde-Watson, Z.; Feeder, N.; Davies, J. E.; Teat, S. J.; Sanders, J. K. M. J. Am. Chem. Soc. 2000, 122, 5286-5293 and references therein.
14. For examples with metal-ligand capsules, see: Zeigler, M.; Brumaghim, J. L.; Raymond, K. N. Angew. Chem., Int. Ed. 2000, 39, 4119-4121. Caulder, D. L.; Raymond, K. N. J. Chem. Soc., Dalton Trans. 1999, 1185-1200. Umemoto, K.; Yamaguchi, K.; Fujita, J. J. Am. Chem. Soc. 2000, 122, 7150-7151. Fujita, M.; Umemoto, K.; Yoshizawa, M.; Fujita, N.; Kusukawa, T.; Biradha, K. Chem. Commun. 2001, 509-518.
15. For examples with metal-ligand capsules, see: Zeigler, M.; Brumaghim, J. L.; Raymond, K. N. Angew. Chem., Int. Ed. 2000, 39, 4119-4121. Caulder, D. L.; Raymond, K. N. J. Chem. Soc., Dalton Trans. 1999, 1185-1200. Umemoto, K.; Yamaguchi, K.; Fujita, J. J. Am. Chem. Soc. 2000, 122, 7150-7151. Fujita, M.; Umemoto, K.; Yoshizawa, M.; Fujita, N.; Kusukawa, T.; Biradha, K. Chem. Commun. 2001, 509-518.
16. For examples with metal-ligand capsules, see: Zeigler, M.; Brumaghim, J. L.; Raymond, K. N. Angew. Chem., Int. Ed. 2000, 39, 4119-4121. Caulder, D. L.; Raymond, K. N. J. Chem. Soc., Dalton Trans. 1999, 1185-1200. Umemoto, K.; Yamaguchi, K.; Fujita, J. J. Am. Chem. Soc. 2000, 122, 7150-7151. Fujita, M.; Umemoto, K.; Yoshizawa, M.; Fujita, N.; Kusukawa, T.; Biradha, K. Chem. Commun. 2001, 509-518.
17. For examples with metal-ligand capsules, see: Zeigler, M.; Brumaghim, J. L.; Raymond, K. N. Angew. Chem., Int. Ed. 2000, 39, 4119-4121. Caulder, D. L.; Raymond, K. N. J. Chem. Soc., Dalton Trans. 1999, 1185-1200. Umemoto, K.; Yamaguchi, K.; Fujita, J. J. Am. Chem. Soc. 2000, 122, 7150-7151. Fujita, M.; Umemoto, K.; Yoshizawa, M.; Fujita, N.; Kusukawa, T.; Biradha, K. Chem. Commun. 2001, 509-518.