Reactivity of osmium tetraoxide towards nitrogen heterocycles: Implications for the molecular recognition of DNA mismatch

Angewandte Chemie - International Edition

Volumn 42, Issue 17, 2003, Pages 1974-1977

  Deubel, Dirk V ^a,b  

^a SWISS FEDERAL INSTITUTE OF TECHNOLOGY   (Switzerland)

^b ACADEMIA SINICA   (Taiwan)

Author keywords

Density functional calculations; Heterocyclic compounds; Hydroxylations; Nucleic acids; Osmium tetraoxide

Indexed keywords

CHARGE TRANSFER; CHEMICAL BONDS; NITROGEN;

CHAMELEON OXIDANTS;

OSMIUM COMPOUNDS;

CARBON; HETEROCYCLIC COMPOUND; NITROGEN DERIVATIVE; NUCLEIC ACID BASE; OSMIUM TETRAOXIDE;

ARTICLE; BASE MISPAIRING; CHEMICAL BOND; DIHYDROXYLATION; MOLECULAR RECOGNITION; QUANTUM CHEMISTRY;

BASE PAIR MISMATCH; DNA; HETEROCYCLIC COMPOUNDS; INDICATORS AND REAGENTS; LIGANDS; MODELS, MOLECULAR; MOLECULAR CONFORMATION; NITROGEN COMPOUNDS; OSMIUM TETROXIDE;

EID: 0037539981     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200250462     Document Type: Article

References (34)

1. a) M. Schröder, Chem. Rev. 1980, 80, 187;
2. b) H. C. Kolb, M. S. Van Nieuwenhze, K. B. Sharpless, Chem. Rev. 1994, 94, 2483;
3. c) M. Beller, K. B. Sharpless in Applied Homogeneous Catalysis (Eds.: B. Cornils, W. A. Herrmann), VCH, Weinheim, 1996, p. 1009;
4. d) H. C. Kolb, K. B. Sharpless in Transition Metals for Organic Synthesis, Vol. 2 (Eds.: M. Beller, C. Bolm), WileyVCH, Weinheim, 1998, p. 219.
5. a) C. Döbler, G. M. Mehltretter, U. Sundermeier, M. Beller, J. Am. Chem. Soc. 2000, 122, 10289;
6. b) S. Y. Jonsson, K. Färnegårdh, J.-E. Bäckvall, J. Am. Chem. Soc. 2001, 123, 1365;
7. 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;
8. 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;
9. d) B. M. Choudary, N. S. Chowdari, K. Jyothi, M. L. Kantam, J. Am. Chem. Soc. 2002, 124, 5341;
10. e) M. A. Andersson, R. Epple, V. V. Fokin, K. B. Sharpless, Angew. Chem. 2002, 114, 490; Angew. Chem. Int. Ed. 2002, 41, 472;
11. e) M. A. Andersson, R. Epple, V. V. Fokin, K. B. Sharpless, Angew. Chem. 2002, 114, 490; Angew. Chem. Int. Ed. 2002, 41, 472;
12. f) C=C cleavage: B. R. Travis, R. S. Narayan, B. Borhan, J. Am. Chem. Soc. 2002, 124, 3824.
13. K. B. Sharpless, Angew. Chem. 2002, 114, 2126; Angew. Chem. Int. Ed. 2002, 41, 2024.
14. K. B. Sharpless, Angew. Chem. 2002, 114, 2126; Angew. Chem. Int. Ed. 2002, 41, 2024.
15. U. Pidun, C. Boehme, G. Frenking, Angew. Chem. 1996, 108, 3008; Angew. Chem. Int. Ed. Engl. 1996, 35, 2817; review: D. V. Deubel, G. Frenking, Acc. Chem. Res. 2003, 36, accepted.
16. U. Pidun, C. Boehme, G. Frenking, Angew. Chem. 1996, 108, 3008; Angew. Chem. Int. Ed. Engl. 1996, 35, 2817; review: D. V. Deubel, G. Frenking, Acc. Chem. Res. 2003, 36, accepted.
17. U. Pidun, C. Boehme, G. Frenking, Angew. Chem. 1996, 108, 3008; Angew. Chem. Int. Ed. Engl. 1996, 35, 2817; review: D. V. Deubel, G. Frenking, Acc. Chem. Res. 2003, 36, accepted.
18. a) L. G. Marzilli, Prog. Inorg. Chem. 1977, 23, 255;
19. b) B. Lippert, Coord. Chem. Rev. 2000, 200, 487.
20. a) D. V. Deubel, G. Frenking, J. Am. Chem. Soc. 1999, 121, 2021;
21. b) D. V. Deubel, J. Sundermeyer, G. Frenking, J. Am. Chem. Soc. 2000, 122, 10101;
22. c) D. V. Deubel, S. Schlecht, G. Frenking, J. Am. Chem. Soc. 2001, 123, 10085. See these studies or the Supporting Information for methodological details. Structures were calculated at the B3LYP/II level, energies at B3LYP/III +.
23. a) J. Florián, J. Leszczynski, J. Am. Chem. Soc. 1996, 118, 3010;
24. b) P. Hobza, J. Sponer, Chem. Rev. 1999, 99, 3247;
25. N. Spackova, I. Berger, J. Sponer, J. Am. Chem. Soc. 1999, 121, 5519.
26. K. P. Gable, F. A. Zhuravlev, J. Am. Chem. Soc. 2002, 124, 3970.
27. S. Dapprich, G. Frenking, J. Phys. Chem. 1995, 99, 9352.
28. a) W. Adam, W. Haas, B. B. Lohray, J. Am. Chem. Soc. 1991,113, 6202;
29. b) H. E. B. Lempers, A. R. I. Garcia, R. A. Sheldon, J. Org. Chem. 1998, 63, 1408;
30. c) G. Boche, J. C. W. Lohrenz, Chem. Rev. 2001, 101, 697;
31. d) D. V. Deubel, J. Org. Chem. 2001, 66, 3790.
32. 3) is less electrophilic, with a d/b ratio of 1.08 in the TS of the [3+2] addition to ethene (d = 0.172, b = 0.158, r = -0.377, Δ = 0.000).
33. Plots of the frontier orbitals of metal oxides are presented in ref. [6a].
34. 4).