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Volumn 10, Issue 10, 2004, Pages 2475-2486

Road maps for nitrogen-transfer catalysis: The challenge of the osmium(VIII)-catalyzed diamination

Author keywords

Density functional calculations; Diamination; Dihydroxylation; Osmium

Indexed keywords

AMINATION; CATALYSIS; CHEMICAL BONDS; ENTHALPY; HYDROXYLATION; OSMIUM; PROBABILITY DENSITY FUNCTION; SUBSTITUTION REACTIONS; THERMODYNAMICS;

EID: 2942609661     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/chem.200305467     Document Type: Article
Times cited : (31)

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    • Recent developments: a) C. Döbler, G. Mehltretter, U. Sundermeier, M. Beller, J. Am. Chem. Soc. 2000, 122, 10 289; b) S. Y. Jonsson, K. Färnegårdh, J.-E. Bäckvall, J. Am. Chem. Soc. 2001, 123, 1365; A. Severeyns, D. E. De Vos, L. Fiermans, F. Verpoort, P. J. Grobet, P. A. Jacobs, Angew. Chem. 2001, 113, 606; Angew. Chem. Int. Ed. 2001, 40, 586; V. V. Fokin, K. B. Sharpless, Angew. Chem. 2001, 113, 3563; Angew. Chem. Int. Ed. 2001, 40, 3455; e) C=C cleavage: B. R. Travis, R. S. Narayan, B. Borhan, J. Am. Chem. Soc. 2002, 124, 3824; f) B. M. Choudary, N. S. Chowdari, K. Jyothi, M. L. Kantam, J. Am. Chem. Soc. 2002, 124, 5341; g) T. J. Donohoe, P. D. Johnson, A. Cowley, M. Keenan, J. Am. Chem. Soc. 2002, 124, 12 934; h) M. A. Andersson, R. Epple, V. V. Fokin, K. B. Sharpless, Angew. Chem. 2002, 114, 490; Angew. Chem. Int. Ed. 2002, 41, 472; R. A. Bhunnoo, Y. L. Hu, D. I. Laine, R. C. D. Brown, Angew. Chem. 2002, 114, 3629; Angew. Chem. Int. Ed. 2002, 41, 3479; j) K. Lee, Y.-H. Kim, S. B. Han, H. Kang, S. Park, W. S. Seo, J. T. Park, B. Kim, S. Chang, J. Am. Chem. Soc. 2003, 125, 6844; k) S. Y. Jonsson, H. Adolfsson, J.-E. Bäckvall, Chem. Eur. J. 2003, 9, 2665.
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    • Recent developments: a) C. Döbler, G. Mehltretter, U. Sundermeier, M. Beller, J. Am. Chem. Soc. 2000, 122, 10 289; b) S. Y. Jonsson, K. Färnegårdh, J.-E. Bäckvall, J. Am. Chem. Soc. 2001, 123, 1365; c) A. Severeyns, D. E. De Vos, L. Fiermans, F. Verpoort, P. J. Grobet, P. A. Jacobs, Angew. Chem. 2001, 113, 606; Angew. Chem. Int. Ed. 2001, 40, 586; V. V. Fokin, K. B. Sharpless, Angew. Chem. 2001, 113, 3563; Angew. Chem. Int. Ed. 2001, 40, 3455; e) C=C cleavage: B. R. Travis, R. S. Narayan, B. Borhan, J. Am. Chem. Soc. 2002, 124, 3824; f) B. M. Choudary, N. S. Chowdari, K. Jyothi, M. L. Kantam, J. Am. Chem. Soc. 2002, 124, 5341; g) T. J. Donohoe, P. D. Johnson, A. Cowley, M. Keenan, J. Am. Chem. Soc. 2002, 124, 12 934; h) M. A. Andersson, R. Epple, V. V. Fokin, K. B. Sharpless, Angew. Chem. 2002, 114, 490; Angew. Chem. Int. Ed. 2002, 41, 472; R. A. Bhunnoo, Y. L. Hu, D. I. Laine, R. C. D. Brown, Angew. Chem. 2002, 114, 3629; Angew. Chem. Int. Ed. 2002, 41, 3479; j) K. Lee, Y.-H. Kim, S. B. Han, H. Kang, S. Park, W. S. Seo, J. T. Park, B. Kim, S. Chang, J. Am. Chem. Soc. 2003, 125, 6844; k) S. Y. Jonsson, H. Adolfsson, J.-E. Bäckvall, Chem. Eur. J. 2003, 9, 2665.
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    • Recent developments: a) C. Döbler, G. Mehltretter, U. Sundermeier, M. Beller, J. Am. Chem. Soc. 2000, 122, 10 289; b) S. Y. Jonsson, K. Färnegårdh, J.-E. Bäckvall, J. Am. Chem. Soc. 2001, 123, 1365; c) A. Severeyns, D. E. De Vos, L. Fiermans, F. Verpoort, P. J. Grobet, P. A. Jacobs, Angew. Chem. 2001, 113, 606; Angew. Chem. Int. Ed. 2001, 40, 586; d) V. V. Fokin, K. B. Sharpless, Angew. Chem. 2001, 113, 3563; Angew. Chem. Int. Ed. 2001, 40, 3455; e) C=C cleavage: B. R. Travis, R. S. Narayan, B. Borhan, J. Am. Chem. Soc. 2002, 124, 3824; f) B. M. Choudary, N. S. Chowdari, K. Jyothi, M. L. Kantam, J. Am. Chem. Soc. 2002, 124, 5341; g) T. J. Donohoe, P. D. Johnson, A. Cowley, M. Keenan, J. Am. Chem. Soc. 2002, 124, 12 934; h) M. A. Andersson, R. Epple, V. V. Fokin, K. B. Sharpless, Angew. Chem. 2002, 114, 490; Angew. Chem. Int. Ed. 2002, 41, 472; R. A. Bhunnoo, Y. L. Hu, D. I. Laine, R. C. D. Brown, Angew. Chem. 2002, 114, 3629; Angew. Chem. Int. Ed. 2002, 41, 3479; j) K. Lee, Y.-H. Kim, S. B. Han, H. Kang, S. Park, W. S. Seo, J. T. Park, B. Kim, S. Chang, J. Am. Chem. Soc. 2003, 125, 6844; k) S. Y. Jonsson, H. Adolfsson, J.-E. Bäckvall, Chem. Eur. J. 2003, 9, 2665.
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    • Travis, B.R.1    Narayan, R.S.2    Borhan, B.3
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    • Choudary, B.M.1    Chowdari, N.S.2    Jyothi, K.3    Kantam, M.L.4
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    • Recent developments: a) C. Döbler, G. Mehltretter, U. Sundermeier, M. Beller, J. Am. Chem. Soc. 2000, 122, 10 289; b) S. Y. Jonsson, K. Färnegårdh, J.-E. Bäckvall, J. Am. Chem. Soc. 2001, 123, 1365; c) A. Severeyns, D. E. De Vos, L. Fiermans, F. Verpoort, P. J. Grobet, P. A. Jacobs, Angew. Chem. 2001, 113, 606; Angew. Chem. Int. Ed. 2001, 40, 586; d) V. V. Fokin, K. B. Sharpless, Angew. Chem. 2001, 113, 3563; Angew. Chem. Int. Ed. 2001, 40, 3455; e) C=C cleavage: B. R. Travis, R. S. Narayan, B. Borhan, J. Am. Chem. Soc. 2002, 124, 3824; f) B. M. Choudary, N. S. Chowdari, K. Jyothi, M. L. Kantam, J. Am. Chem. Soc. 2002, 124, 5341; g) T. J. Donohoe, P. D. Johnson, A. Cowley, M. Keenan, J. Am. Chem. Soc. 2002, 124, 12 934; h) M. A. Andersson, R. Epple, V. V. Fokin, K. B. Sharpless, Angew. Chem. 2002, 114, 490; Angew. Chem. Int. Ed. 2002, 41, 472; R. A. Bhunnoo, Y. L. Hu, D. I. Laine, R. C. D. Brown, Angew. Chem. 2002, 114, 3629; Angew. Chem. Int. Ed. 2002, 41, 3479; j) K. Lee, Y.-H. Kim, S. B. Han, H. Kang, S. Park, W. S. Seo, J. T. Park, B. Kim, S. Chang, J. Am. Chem. Soc. 2003, 125, 6844; k) S. Y. Jonsson, H. Adolfsson, J.-E. Bäckvall, Chem. Eur. J. 2003, 9, 2665.
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    • Donohoe, T.J.1    Johnson, P.D.2    Cowley, A.3    Keenan, M.4
  • 25
    • 0037784368 scopus 로고    scopus 로고
    • Recent developments: a) C. Döbler, G. Mehltretter, U. Sundermeier, M. Beller, J. Am. Chem. Soc. 2000, 122, 10 289; b) S. Y. Jonsson, K. Färnegårdh, J.-E. Bäckvall, J. Am. Chem. Soc. 2001, 123, 1365; c) A. Severeyns, D. E. De Vos, L. Fiermans, F. Verpoort, P. J. Grobet, P. A. Jacobs, Angew. Chem. 2001, 113, 606; Angew. Chem. Int. Ed. 2001, 40, 586; d) V. V. Fokin, K. B. Sharpless, Angew. Chem. 2001, 113, 3563; Angew. Chem. Int. Ed. 2001, 40, 3455; e) C=C cleavage: B. R. Travis, R. S. Narayan, B. Borhan, J. Am. Chem. Soc. 2002, 124, 3824; f) B. M. Choudary, N. S. Chowdari, K. Jyothi, M. L. Kantam, J. Am. Chem. Soc. 2002, 124, 5341; g) T. J. Donohoe, P. D. Johnson, A. Cowley, M. Keenan, J. Am. Chem. Soc. 2002, 124, 12 934; h) M. A. Andersson, R. Epple, V. V. Fokin, K. B. Sharpless, Angew. Chem. 2002, 114, 490; Angew. Chem. Int. Ed. 2002, 41, 472; R. A. Bhunnoo, Y. L. Hu, D. I. Laine, R. C. D. Brown, Angew. Chem. 2002, 114, 3629; Angew. Chem. Int. Ed. 2002, 41, 3479; j) K. Lee, Y.-H. Kim, S. B. Han, H. Kang, S. Park, W. S. Seo, J. T. Park, B. Kim, S. Chang, J. Am. Chem. Soc. 2003, 125, 6844; k) S. Y. Jonsson, H. Adolfsson, J.-E. Bäckvall, Chem. Eur. J. 2003, 9, 2665.
    • (2002) Angew. Chem. , vol.114 , pp. 490
    • Andersson, M.A.1    Epple, R.2    Fokin, V.V.3    Sharpless, K.B.4
  • 26
    • 0036462501 scopus 로고    scopus 로고
    • Recent developments: a) C. Döbler, G. Mehltretter, U. Sundermeier, M. Beller, J. Am. Chem. Soc. 2000, 122, 10 289; b) S. Y. Jonsson, K. Färnegårdh, J.-E. Bäckvall, J. Am. Chem. Soc. 2001, 123, 1365; c) A. Severeyns, D. E. De Vos, L. Fiermans, F. Verpoort, P. J. Grobet, P. A. Jacobs, Angew. Chem. 2001, 113, 606; Angew. Chem. Int. Ed. 2001, 40, 586; d) V. V. Fokin, K. B. Sharpless, Angew. Chem. 2001, 113, 3563; Angew. Chem. Int. Ed. 2001, 40, 3455; e) C=C cleavage: B. R. Travis, R. S. Narayan, B. Borhan, J. Am. Chem. Soc. 2002, 124, 3824; f) B. M. Choudary, N. S. Chowdari, K. Jyothi, M. L. Kantam, J. Am. Chem. Soc. 2002, 124, 5341; g) T. J. Donohoe, P. D. Johnson, A. Cowley, M. Keenan, J. Am. Chem. Soc. 2002, 124, 12 934; h) M. A. Andersson, R. Epple, V. V. Fokin, K. B. Sharpless, Angew. Chem. 2002, 114, 490; Angew. Chem. Int. Ed. 2002, 41, 472; R. A. Bhunnoo, Y. L. Hu, D. I. Laine, R. C. D. Brown, Angew. Chem. 2002, 114, 3629; Angew. Chem. Int. Ed. 2002, 41, 3479; j) K. Lee, Y.-H. Kim, S. B. Han, H. Kang, S. Park, W. S. Seo, J. T. Park, B. Kim, S. Chang, J. Am. Chem. Soc. 2003, 125, 6844; k) S. Y. Jonsson, H. Adolfsson, J.-E. Bäckvall, Chem. Eur. J. 2003, 9, 2665.
    • (2002) Angew. Chem. Int. Ed. , vol.41 , pp. 472
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    • 2942553093 scopus 로고    scopus 로고
    • Recent developments: a) C. Döbler, G. Mehltretter, U. Sundermeier, M. Beller, J. Am. Chem. Soc. 2000, 122, 10 289; b) S. Y. Jonsson, K. Färnegårdh, J.-E. Bäckvall, J. Am. Chem. Soc. 2001, 123, 1365; c) A. Severeyns, D. E. De Vos, L. Fiermans, F. Verpoort, P. J. Grobet, P. A. Jacobs, Angew. Chem. 2001, 113, 606; Angew. Chem. Int. Ed. 2001, 40, 586; d) V. V. Fokin, K. B. Sharpless, Angew. Chem. 2001, 113, 3563; Angew. Chem. Int. Ed. 2001, 40, 3455; e) C=C cleavage: B. R. Travis, R. S. Narayan, B. Borhan, J. Am. Chem. Soc. 2002, 124, 3824; f) B. M. Choudary, N. S. Chowdari, K. Jyothi, M. L. Kantam, J. Am. Chem. Soc. 2002, 124, 5341; g) T. J. Donohoe, P. D. Johnson, A. Cowley, M. Keenan, J. Am. Chem. Soc. 2002, 124, 12 934; h) M. A. Andersson, R. Epple, V. V. Fokin, K. B. Sharpless, Angew. Chem. 2002, 114, 490; Angew. Chem. Int. Ed. 2002, 41, 472; i) R. A. Bhunnoo, Y. L. Hu, D. I. Laine, R. C. D. Brown, Angew. Chem. 2002, 114, 3629; Angew. Chem. Int. Ed. 2002, 41, 3479; j) K. Lee, Y.-H. Kim, S. B. Han, H. Kang, S. Park, W. S. Seo, J. T. Park, B. Kim, S. Chang, J. Am. Chem. Soc. 2003, 125, 6844; k) S. Y. Jonsson, H. Adolfsson, J.-E. Bäckvall, Chem. Eur. J. 2003, 9, 2665.
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    • Recent developments: a) C. Döbler, G. Mehltretter, U. Sundermeier, M. Beller, J. Am. Chem. Soc. 2000, 122, 10 289; b) S. Y. Jonsson, K. Färnegårdh, J.-E. Bäckvall, J. Am. Chem. Soc. 2001, 123, 1365; c) A. Severeyns, D. E. De Vos, L. Fiermans, F. Verpoort, P. J. Grobet, P. A. Jacobs, Angew. Chem. 2001, 113, 606; Angew. Chem. Int. Ed. 2001, 40, 586; d) V. V. Fokin, K. B. Sharpless, Angew. Chem. 2001, 113, 3563; Angew. Chem. Int. Ed. 2001, 40, 3455; e) C=C cleavage: B. R. Travis, R. S. Narayan, B. Borhan, J. Am. Chem. Soc. 2002, 124, 3824; f) B. M. Choudary, N. S. Chowdari, K. Jyothi, M. L. Kantam, J. Am. Chem. Soc. 2002, 124, 5341; g) T. J. Donohoe, P. D. Johnson, A. Cowley, M. Keenan, J. Am. Chem. Soc. 2002, 124, 12 934; h) M. A. Andersson, R. Epple, V. V. Fokin, K. B. Sharpless, Angew. Chem. 2002, 114, 490; Angew. Chem. Int. Ed. 2002, 41, 472; i) R. A. Bhunnoo, Y. L. Hu, D. I. Laine, R. C. D. Brown, Angew. Chem. 2002, 114, 3629; Angew. Chem. Int. Ed. 2002, 41, 3479; j) K. Lee, Y.-H. Kim, S. B. Han, H. Kang, S. Park, W. S. Seo, J. T. Park, B. Kim, S. Chang, J. Am. Chem. Soc. 2003, 125, 6844; k) S. Y. Jonsson, H. Adolfsson, J.-E. Bäckvall, Chem. Eur. J. 2003, 9, 2665.
    • (2002) Angew. Chem. Int. Ed. , vol.41 , pp. 3479
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    • note
    • Osmate esters can be stabilized by the coordination of additional ligands and by the formation of metallabicycles; see ref. [4] for details.
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    • 2 as the non-oxidative N donor.
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    • 3 bond in the presence of four very strong Os=O bonds; see, for example: a) D. V. Deubel, J. Sundermeyer, G. Frenking, Inorg. Chem. 2000, 39, 2314; b) D. V. Deubel, J. Sundermeyer, G. Frenking, Org. Lett. 2001, 3, 329; c) D. V. Deubel, J. Sundermeyer, G. Frenking, Eur. J. Inorg. Chem. 2001, 1819.
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    • -1 for imidodioxoosma-2,5-diazolidine. If one wishes to consider ammoniolysis rather than hydrolysis and subsequent oxo-imido exchange, one may simply add the reaction free enthalpies of the latter two reactions.


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