Stereoselective syntheses of functionalized cyclic ethers via (Schiff-base)vanadium(V)-catalyzed oxidations

Pure and Applied Chemistry

Volumn 77, Issue 9, 2005, Pages 1559-1574

  Hartung, Jens ^a  

^a Rheinland Pfälzische Technische Universität Kaiserslautern Landau   (Germany)

Author keywords

Bromide; Bromoperoxidase; Oxidation; tert butyl hydroperoxide; Tetrahydrofuran; Tetrahydropyran; Vanadium

Indexed keywords

EID: 26644472441     PISSN: 00334545     EISSN: None     Source Type: Journal    
DOI: 10.1351/pac200577091559     Document Type: Conference Paper

References (58)

1. J. W. Blunt, B. R. Copp, M. H. G. Munro, P. T. Northcote, M. R. Prinsep. J. Nat. Prod. 21, 1 (2004).
2. M. M. Faul and B. E. Huff. Chem. Rev. 100, 2407 (2000).
3. G. W. Gribble. Acc. Chem. Res. 31, 141 (1998).
4. H. Avedissian, S. C. Sinha, A. Yazbak, A. Sinha, P. Neogi, S. C. Sinha, E. Keinan. J. Org. Chem. 65, 6035 (2000).
5. Z.-M. Wang, S.-K. Tian, M. Shi. Eur. J. Org. Chem. 349 (2000).
6. M. Cueto and J. Darias. Tetrahedron 52, 5899 (1996).
7. J.-C. Harmange and B. Figadère. Tetrahedron: Asymmetry 4, 1711 (1993).
8. M. H. D. Postema. Tetrahedron 48, 854 (1992).
9. T. L. B. Boivin. Tetrahedron 43, 3309 (1987).
10. J. Hartung and M. Greb. J. Organomet. Chem. 661, 67 (2002).
11. S. Tang and R. M. Kennedy. Tetrahedron Lett. 33, 5299 (1992).
12. T. B. Towne and F. E. McDonald. J. Am. Chem. Soc. 119, 6022 (1997).
13. J. Hartung and P. Schmidt. Selective Reactions of Metal-activated Molecules, H. Werner and P. Schreier (Eds.), p. 65, Vieweg, Braunschweig (1998).
14. D. Klimetzek, J. Bartels, W. Francke. Z. Ang. Ent. 107, 518 (1989).
15. A. Miyazawa, H. Nankai, H. Kameoka. Phytochemistry 39, 1077 (1995).
16. N. M. Phuong, T. V. Sung, A. Porzel, J. Schmidt, K. Merzweiler, G. Adam. Phytochemistry 52, 1725 (1999).
17. T. Kusumi, H. Uchida, Y. Inouye, M. Ishitsuka, H. Yamamoto H. Kakisawa. J. Org. Chem. 52, 4597 (1987).
18. C. O. Willits, C. Ricciuti, H. B. Knight, D. Swern. Anal. Chem. 24, 785 (1952).
19. N. A. Milas and S. A. Harris. J. Am. Chem. Soc. 60, 2434 (1938).
20. R. A. Sheldon. The Chemistry of Functional Groups, Peroxides, S. Patai, (Ed.), Chap. 6, John Wiley, Chichester (1983).
21. K. B. Sharpless and T. R. Verhoeven. Aldrichim. Acta 12, 63 (1979).
22. S. Drees, M. Greb, J. Hartung, P. Schmidt. Peroxide Chemistry, W. Adam (Ed.), Chap. 5.2, Wiley-VCH, Weinheim (2000).
23. H. Mimoun, M. Mignard, P. Brechot, L. Saussine. J. Am. Chem. Soc. 108, 3711 (1986).
24. L. J. Theriot, G. O. Carlisle, H. J. Hu. J. Inorg. Nucl. Chem. 31, 2841 (1969).
25. G. Liu, D. Cogan, J. A. Ellman. J. Am. Chem. Soc. 119, 9913 (1997).
26. M. Bashipoor, H. Schmidt, C. Schulzke, D. Rehder. Chem. Ber./Receuil 130, 651 (1997).
27. M. J. Clague, N. L. Keder, A. Butler. Inorg. Chem. 32, 4754 (1993).
28. J. Hartung, S. Drees, M. Greb, P. Schmidt, I. Svoboda, H. Fuess, A. Murso, D. Stalke. Eur. J. Org. Chem. 2388 (2003).
29. M. Greb, J. Hartung, F. Köhler, K. Špehar, R. Kluge, R. Csuk. Eur. J. Org. Chem. 3799 (2004).
30. M. F. Brown, B. R. Cook, T. E. Sloan. Inorg. Chem. 14, 1273 (1975).
31. W. Liebscher and J. Neels. Nomenklatur in der Anorganischen Chemie/International Union of Pure and Applied Chemistry (IUPAC), p. 224, VCH, Weinheim (1990).
32. 4 axis. A C-configuration is associated with a clockwise arrangement of the four atoms in the plane of the square pyramid in decreasing CIP-hierarchy 1-2-3-4. If the atoms with CIP hierarchy 1 and 2 are bound in opposite and not in vicinal coordination sites, the direction for configuration assignment that proceeds via the atom with the hierarchy 3 is preferred thus leading to the sequence 1-3-2 instead of going from 1 via 4 to 2 and then on to 3. The latter error unfortunately has been made in earlier contributions from my group [10,22,28]. In all instances, the opposite configuration from of what has been reported in these papers is correct in order to agree with the IUPAC convention.
33. W. R. Scheidt, M. D. Collins, J. L. Hoard. J. Am. Chem. Soc. 93, 3873 (1971).
34. R. Fulwood, H. Schmidt, D. Rehder. J. Chem. Soc., Chem. Commun. 1443 (1995).
35. M. Kojima, K. Nakajima, M. Tsuchimoto, M. Tanaka, T. Suzuta, Y. Yoshikawa, J. Fujita. Chem. Lett. 949 (1994).
36. S. Mondal, S. P. Rath, K. K. Rajak, A. Chakravorty. Inorg. Chem. 37, 1713 (1998).
37. J. C. Pessoa, I. Tomaz, R. T. Henriques. Inorg. Chim. Acta 356, 121 (2003).
38. J. Hartung and P. Schmidt. Synlett 367 (2000).
39. P. Schmidt. Thesis, Universität Würzburg, Würzburg (2002).
40. W. Adam, W. Haas, B. B. Lohray. J. Am. Chem. Soc. 113, 6202 (1991).
41. D. V. Deubel. J. Org. Chem. 66, 2686 (2001).
42. L. P. Hager, D. R. Morris, F. S. Brown, H. Everwein. J. Biol. Chem. 241, 1769 (1966).
43. J. Hartung and A. Ludwig. Manuscript in preparation.
44. J. Hartung, S. Drees, B. Geiss, P. Schmidt. Synlett 223 (2003).
45. K. B. Sharpless and R. C. Michaelson. J. Am. Chem. Soc. 95, 6136 (1973).
46. Z.-X. Wang and Y. Shi. J. Org. Chem. 63, 3099 (1998).
47. J. L. Von dem Bussche-Huennefeld and D. Seebach. Tetrahedron 48, 5719 (1992).
48. Y. Shi. Acc. Chem. Res. 37, 488 (2004).
49. U. Bora, G. Bose, M. K. Chaudhuri, S. S. Dhar, R. Gopinath, A. T. Kahn, B. K. Patel. Org. Lett. 2, 247 (2000).
50. P. A. Barlett. Asymmetric Synthesis, Vol. 3, J. D. Morrison (Ed.), Academic Press, New York (1984).
51. A. H. Hoveyda, D. A. Evans, G. C. Fu. Chem. Rev. 93, 1307 (1993).
52. C. W. Jones. Applications of Hydrogen Peroxide and Derivatives, J. H. Clark (Series Ed.), RSC Clean Technology Monographs, Cambridge (1999).
53. J. Hartung, P. Kunz, S. Laug, P. Schmidt. Synlett 51 (2003).
54. K. Mori, M. Komatsu, M. Kido, K. Nakagawa. Tetrahedron 42, 523 (1986).
55. J. Hartung and M. Greb. Tetrahedron Lett. 44, 6091 (2003).
56. M. E. Jung, B. T. Fahr, D. C. D'Amico. J. Org. Chem. 63, 2982 (1998).
57. P. H. J. Carlsen, T. Katsuki, V. S. Martin, K. B. Sharpless. J. Org. Chem. 46, 3936 (1981).
58. K. Takai, K. Nitta, K. Utimoto. J. Am. Chem. Soc. 108, 7408 (1986).