From Cobalt(II)-Activated Molecular Oxygen to Hydroxymethyl-Substituted Tetrahydrofurans

Activating Unreactive Substrates: The Role of Secondary Interactions

Volumn , Issue , 2009, Pages 379-396

  Menéndez Pérez, Bárbara ^a   Schuch, Dominik ^a   Hartung, Jens ^a  

^a University of Koblenz Landau   (Germany)

Author keywords

Aerobic oxidation; Cobalt activated; Magnosalicin; Oxidative cyclization; Tetrahydrofurans; Unsaturated alcohols

Indexed keywords

EID: 84890998393     PISSN: None     EISSN: None     Source Type: Book    
DOI: 10.1002/9783527625468.ch21     Document Type: Chapter

References (52)

1. The following abbreviations were used: BDE = bond dissociation energy CAB = cobalt/acetate/bromide; de = diastereomeric excess; dr = diastereomeric ratio; er = enantiomeric ratio; ms = molecular sieve; T = twist conformer of tetrahydrofuran; TBHP = tert-butyl hydroperoxide; ZPVE = zero-point vibrational energy.
2. Werner, A. and Mylius, A.Z.Z. (1898) Zeitschrift fur Anorganische und Allgemeine Chemie, 16, 245-267.
3. Tsumaki, T. (1938) Bulletin of the Chemical Society of Japan, 13, 252-260.
4. Samándi, L.I. (2003) in Advances in Catalytic Activation of Dioxygen by Metal Complexes, (ed. L.I. Simándi), Kluwer Academic Publishers, Dordrecht, pp. 265-328.
5. Drago, R.S. and Corden, B.B. (1980) Accountsof Chemical Research, 13, 353-360.
6. Henrici-Olive,́ G. and Oliv,é S. (1974) Angewandte Chemie, 86, 1-12.
7. Henrici-Oliv,é G. and Oliv,é S. (1974) Angewandte Chemie-International Edition, 13, 29-38.
8. Zhang, M., van Eldik, R., Espenson, J.H. and Bakac, A. (1994) Inorganic Chemistry, 33, 130-133.
9. Nishinaga, A., Tomita, H. and Matsuura, T. (1980) Tetrahedron Letters, 21, 4853-4854.
10. Zombeck, A., Drago, R.S., Corden, B. and Gaul, J.H. (1981) Journal of the American Chemical Society, 103, 7530-7585.
11. Vogt, L.H., Jr. Wirth, J.G. and Finkbeiner, H.L. (1969) The Journal of Organic Chemistry, 34, 273-277.
12. Freemann, F. (1986) in Organic Synthesis by Oxidations with Metal Compounds, (eds W.J. Mijs and De Jonge C.R.H.), Plenum Press, New York, pp. 315-371.
13. Takai, T., Hata, E., Yorozu, K. and Mukaiyama, T. (1992) Chemistry Letters, 2077-2080.
14. Tang, Q., Zhang, Q., Wu, H. and Wang, Y. (2005) Journal of Molecular Catalysis A, 230, 384-397.
15. Hunter, R., Turner, P. and Rimmer, S. (2000) Synthetic Communications, 30, 4461-4466.
16. Punniyamurthy, T., Bhatis, B., Reddy, M.M., Maikap, G.C. and Iqbal, J. (1997) Tetrahedron, 53, 7649-7670.
17. Mukaiyama, T., Yorozu, K., Takai, T. and Yamada, T. (1993) Chemistry Letters, 439-442.
18. Hamilton, D.E., Drago, R.S. and Zombeck, A. (1987) Journal of the American Chemical Society, 109, 374-379.
19. Partenheimer, W. (2006) Advanced Synthesis and Catalysis, 348, 559-568.
20. Inoki, S. and Mukaiyama, T. (1990) Chemistry Letters, 67-70.
21. Wang, Z.-M., Tian, S.-K. and Shi, M. (1999) Tetrahedron Letters, 40, 977-980.
22. Wang, Z.-M., Tian, S.-K. and Shi, M. (1999) Tetrahedron: Asymmetry, 10, 667-670.
23. Gribble, G.W. (1998) Accounts of Chemical Research, 31, 141-152.
24. Faul, M.M. and Huff, B.E. (2000) Chemical Reviews, 100, 2407-2473.
25. Hartung, J. and Greb, M. (2002) Journal of Organometallic Chemistry, 661, 67-84.
26. Hartung, J., Drees, S., Greb, M., Schmidt, P., Svoboda, I., Fuess, H., Murso, A. and Stalke, D. (2003) European Journal of Organic Chemistry, 2388-2408.
27. Mori, K., Komatsu, M., Kido, M. and Nakagawa, K. (1986) Tetrahedron, 42, 523-528.
28. Greb, M., Hartung, J., Köhler, F., Špehar, K., Kluge, R. and Csuk, R. (2004) European Journal of Organic Chemistry, 3799-3812.
29. Sheldon, R.A. (1993) Topics in Current Chemistry, 164, 23-43.
30. Kaim, W. and Schwederski, B. (1991) Bioanorganische Chemie, Teubner, Stuttgart, pp. 87-134.
31. Luo, Y.-R. (2003) Handbook of Bond Dissociation Energies in Organic Compounds, CRC Press, Boca Raton.
32. Brix, P. and Herzberg, G. (1953) Journal of Chemical Physics, 21, 2240.
33. Mukaiyama, T. and Yamada, T. (1995) Bulletin of the Chemical Society of Japan, 68, 17-35.
34. Frisch, M.J., Trucks, G.W., Schlegel, H.B., Scuseria, G.E., Robb, M.A., Cheeseman, J.R., Zakrzewski, V.G., Montgomery, J.A., Jr. Stratmann, R.E., Burant, J.C., Dapprich, S., Millam, J.M., Daniels, A.D., Kudin, K.N., Strain, M.C., Farkas, O., Tomasi, J., Barone, V., Cossi, M., Cammi, R., Mennucci, B., Pomelli, C., Adamo, C., Clifford, S., Ochterski, J., Petersson, G.A., Ayala, P.Y., Cui, Q., Morokuma, K., Malick, D.K., Rabuck, A.D., Raghavachari, K., Foresman, J.B., Cioslowski, J., Ortiz, J.V., Baboul, A.G., Stefanov, B.B., Liu, G., Liashenko, A., Piskorz, P., Komaromi, I., Gomperts, R., Martin, R.L., Fox, D.J., Keith, T., Al-Laham, M.A., Peng, C.Y., Nanayakkara, A., Gonzalez, C., Challacombe, M., Gill, P.M.W., Johnson, B., Chen, W., Wong, M.W., Andres, J.L., Gonzalez, C., Head-Gordon, M., Replogle, E.S. and Pople J.A. (1998) Gaussian 98, Revision A.7, Gaussian, Inc., Pittsburgh PA.
35. Schmidt, M.W., Truong, P.N. and Gordon, M.S. (1987) Journal of the American Chemical Society, 109, 5217-5227.
36. Holm, R.H. and Cotton, F.A. (1960) Journal of Inorganic and Nuclear Chemistry, 15, 63-66.
37. Lintwedt, R.L. and Fatta, A.M. (1968) Inorganic Chemistry, 7, 2489-2495.
38. Kato, K., Yamada, T., Takai, T., Inoki, S. and Isayama, S. (1990) Bulletin of the Chemical Society of Japan, 63, 179-186.
39. Hsu, E.C. and Holzwarth, G. (1973) Journal of the American Chemical Society, 95, 6902-6906.
40. Drees, S. (2002) Dissertation, Universtität Würzburg.
41. Menéndez, B., Schuch, D. and Hartung, J. (2008) Organic Biomolecular Chemistry, 6, 3532-3541.
42. Hartung, J. and Fink, K. unpublished results.
43. Brunel, J.-M., Pardigon, O., Maffei, M. and Buono, G. (1992) Tetrahedron: Asymmetry, 3, 1243-1246.
44. Holleman, A.F. and Wiberg, E. (1995) Lehrbuch der Anorganischen Chemie, de Gruyter, 101. Auflage, Berlin, pp. 1548-1574.
45. Sheldon, R.A. and Kochi, J.K. (1981) Metal-Catalyzed Oxidations of Organic Compounds, Academic Press, New York.
46. Lipari, F. and Swarin, S.J. (1982) Journal of Chromatography, 247, 297-306.
47. Wieland, G. (1985) Wasserbestimmung durch Karl-Fischer-Titration, GIT-Verlag, Darmstadt.
48. Zombeck, A., Hamilton, D.E. and Drago, R.S. (1982) Journal of the American Chemical Society, 104, 6782-6784.
49. Tang, S. and Kennedy, R.M. (1992) Tetrahedron Letters, 33, 5299-5302.
50. Lempers, H.E.B., Ripollès i Garcia, A. and Sheldon, R.A. (1998) The Journal of Organic Chemistry, 63, 1408-1413.
51. Hartung, J., Gottwald, T. and Špehar, K. (2002) Synthesis, 1469-1498.
52. Hartung, J., Kopf, T.M., Kneuer, R. and Schmidt, P. (2001) ComptesRendusAcademic de Sciences Paris Chimie/Chemistry, 649-666.