Cis-2,6-Bis-(methanolate)-piperidine oxovanadium(V) complexes as catalysts for oxidative alkenol cyclization by tert-butyl hydroperoxide

Inorganica Chimica Acta

Volumn 420, Issue , 2014, Pages 120-134

  Dönges, Maike ^a   Amberg, Matthias ^a   Stapf, Georg ^a   Kelm, Harald ^a   Bergsträßer, Uwe ^a   Hartung, Jens ^a  

^a University of Koblenz Landau   (Germany)

Author keywords

Catalysis; Oxepane; Oxidation; Tetrahydrofuran; Tetrahydropyran; Vanadium

Indexed keywords

CATALYSIS; CATALYSTS; CYCLIZATION; OXIDATION; PROPANOL; VANADIUM;

COMPLEX FORMATIONS; MINOR PRODUCTS; OXEPANE; OXIDATIVE CYCLIZATION; TERT-BUTYLHYDROPEROXIDE; TETRA-HYDROFURAN; TETRAHYDROPYRAN; VANADIUM CATALYST;

VANADIUM COMPOUNDS;

EID: 84903381420     PISSN: 00201693     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.ica.2014.02.007     Document Type: Article

References (56)

1. F. Freeman Oxidation by Vanadium Compounds W.J. Mijs, C.R.H. De Jonge, Organic Synthesis by Oxidations with Metal Compounds 1986 Plenum Press New York 1
2. R.A. Sheldon Aspects of Homogeneous Catalysis fourth ed. 1981 Reidel Publishing Dordrecht 3
3. R.A. Sheldon The Chemistry of Functional Groups: Peroxides 1983 John Wiley Chichester 161
4. K.B. Sharpless, and K.C. Michaelson J. Am. Chem. Soc. 95 1973 6136
5. W. Zhang, A. Basak, Y. Kosugi, Y. Hoshino, and H. Yamamoto Angew. Chem. 117 2005 463
6. T. Nakata, G. Schmid, B. Vranesic, M. Okigawa, T. Smith-Palmer, and Y. Kishi J. Am. Chem. Soc. 100 1978 2933
7. J. Hartung, and M. Greb J. Organomet. Chem. 661 2002 67
8. J. Hartung, S. Drees, M. Greb, P. Schmidt, I. Svoboda, H. Fuess, A. Murso, and D. Stalke Eur. J. Org. Chem. 2003 2388
9. G.E. Veitch, E. Beckmann, B.J. Burke, A. Boyer, C. Ayats, and S.V. Ley Angew. Chem. 119 2007 7777
10. K. Mori, M. Komatsu, M. Kido, and K. Nakagawa Tetrahedron 42 1986 523
11. J. Rodríguez-López, F.P. Crisóstomo, N. Ortega, M. López-Rodríguez, V.S. Martín, and T. Martín Angew. Chem., Int. Ed. 52 2013 3659
12. R. Ballardini, V. Balzani, A. Credi, M.T. Gandolfi, and M. Venturi Acc. Chem. Res. 34 2001 445
13. C.J. Pedersen, and H.K. Frensdorff Angew. Chem. 84 1972 16
14. B.R. Kusche, A.E. Smith, M.A. McGuirl, and N.D. Priestley J. Am. Chem. Soc. 131 2009 17155
15. N.A. Milas, and S.A. Harris J. Am. Chem. Soc. 60 1938 2434
16. K.B. Sharpless, and T.R. Verhoeven Aldrichim. Acta 12 1979 63
17. J.G. Hill, B.E. Rossiter, and K.B. Sharpless J. Org. Chem. 48 1983 3607
18. D. Wischang, O. Brücher, and J. Hartung Coord. Chem. Rev. 255 2011 2204
19. V. Conte, F. Di Furia, and G. Modena J. Org. Chem. 53 1988 1665
20. S.W. Wright, D.L. Haagemann, A.S. Wright, and L.D. McClure Tetrahedron Lett. 42 1997 7345
21. C.D. Crans, J.J. Smee, E. Gaidamauskas, and L. Yang Chem. Rev. 104 2004 849
22. T. Hirao Chem. Rev. 97 1997 2707
23. W. Zhang, and H. Yamamoto J. Am. Chem. Soc. 129 2007 286
24. Y. Hoshino, and H. Yamamoto J. Am. Chem. Soc. 122 2000 10452
25. N. Makita, Y. Hoshino, and H. Yamamoto Angew. Chem. 115 2003 971
26. J. Hartung Pure Appl. Chem. 77 2005 1559
27. D. Klimetzek, J. Bartels, and W. Francke J. Appl. Entomol. 107 1989 518
28. T. Kusumi, H. Uchida, Y. Inouye, M. Ishitsuka, H. Yamamoto, and H. Kakisawa J. Org. Chem. 52 1987 4597
29. S. Dötterl, D. Burkhardt, B. Weißbecker, A. Jürgens, and A. Mosandl J. Chromatogr. A 1113 2006 231
30. K. Suenaga, T. Shibata, N. Takada, H. Kigushi, and K. Yamada J. Nat. Prod. 61 1998 515
31. A. Archelas, and R. Furstoss Tetrahedron Lett. 33 1992 5241
32. P. Henne, R. Thiericke, S. Grabley, K. Hütter, J. Wink, E. Jurkiewicz, and A. Zeeck Lieb. Ann. Chem. 12 1993 565
33. J. Hartung, T. Gottwald, and K. Špehar Synthesis 11 2002 1469
34. P. Fries, D. Halter, A. Kleinschek, and J. Hartung J. Am. Chem. Soc. 133 2011 3906
35. J. Hartung, Y. Dumont, M. Greb, D. Hach, F. Köhler, H. Schulz, M. Časný, D. Rehder, and H. Vilter Pure Appl. Chem. 81 2009 1251
36. M. Amberg, M. Dönges, G. Stapf, J. Hartung, manuscript submitted.
37. J. Hartung, A. Ludwig, M. Demary, and G. Stapf K. Kustin, J.C. Pessoa, D.C. Crans, Vanadium: The Versatile Metal 2007 American Chemical Society Washington DC 38 Chapter 4
38. S. Drees, M. Greb, J. Hartung, and P. Schmidt W. Adam, Peroxide Chemistry - Mechanistic and Preparative Aspects of Oxygen Transfer 2000 Wiley-VCH Weinheim
39. A. Klein, S. Elmas, and K. Butsch Eur. J. Inorg. Chem. 15 2009 2271
40. R. Chênevert, and M. Dickman J. Org. Chem. 61 1996 3332
41. M. Amberg, U. Bergsträßer, G. Stapf, and J. Hartung J. Org. Chem. 73 2008 3907
42. M. Amberg, I. Kempter, U. Bergsträßer, G. Stapf, and J. Hartung Tetrahedron: Asymmetry 22 2011 752
43. W. Prandtl, and L. Hess Z. Anorg. Chem. 82 1913 103
44. J. Spandl, I. Brüdgam, and H. Hartl Z. Anorg. Allg. Chem. 626 2000 2125
45. M.J. Clague, N.L. Keder, and A. Butler Inorg. Chem. 32 1993 4754
46. C.J. Ballhausen, and H.B. Gray Inorg. Chem. 1 1962 111
47. D. Rehder Angew. Chem. 103 1991 152
48. J.K. Kochi J. Am. Chem. Soc. 84 1962 1193
49. E. Montaudon, X. Lubeigt, and B. Maillard J. Chem. Soc., Perkin Trans. 1 1991 1531
50. W.P. Jackson Synlett 1990 536
51. D.E. Bissing, C.A. Matuszak, and W.E. McEwen J. Am. Chem. Soc. 86 1964 3824
52. J. Hartung, and P. Schmidt Synlett 2000 367
53. E.L. Eliel, and S.H. Wilen Organische Stereochemie 1998 Wiley-VCH Weinheim p. 421
54. R.L. Farmer, and F.L. Urbach Inorg. Chem. 11 1970 2562
55. T. Katsuki, and K.B. Sharpless J. Am. Chem. Soc. 102 1980 5974
56. J. Hartung, U. Bergsträsser, K. Daniel, N. Schneiders, I. Svoboda, and H. Fuess Tetrahedron 65 2009 2567