Multinuclear NMR study of the reactive intermediates in enantioselective epoxidations of allylic alcohols catalyzed by a vanadium complex derived from a planar-chiral hydroxamic acid

New Journal of Chemistry

Volumn 27, Issue 3, 2003, Pages 609-614

  Bryliakov, Konstantin P ^a   Talsi, Evgenii P ^a   Kühn, Toralf ^b   Bolm, Carsten ^b  

^a BORESKOV INSTITUTE OF CATALYSIS   (Russian Federation)

^b RWTH AACHEN UNIVERSITY   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

ALLYL ALCOHOL; CARBON 13; EPOXIDE; GERANIOL; HYDROXAMIC ACID; METAL COMPLEX; OXYGEN 17; PARACYCLOPHANE DERIVATIVE; TERT BUTYL HYDROPEROXIDE; VANADIUM DERIVATIVE;

ARTICLE; ASYMMETRIC CATALYSIS; CARBON NUCLEAR MAGNETIC RESONANCE; CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; CHIRALITY; COMPLEX FORMATION; ENANTIOSELECTIVITY; EPOXIDATION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PRIORITY JOURNAL;

EID: 0037352252     PISSN: 11440546     EISSN: None     Source Type: Journal    
DOI: 10.1039/b208748k     Document Type: Article

References (52)

1. (a) T. Katsuki and K. B. Sharpless, J. Am. Chem. Soc., 1980, 102, 5974;
2. Y. Gao, R. M. Hanson, J. M. Klunder, S. Y. Ko, H. Masamune and K. B. Sharpless. J. Am. Chem. Soc., 1987, 109, 5765.
3. (a) R. A. Johnson and K. B. Sharpless, in Catalytic Asymmetric Synthesis, ed. I. Ojima, VCH, New York, 1993, p. 103;
4. (b) X. Wen and I. Ojima, in Catalytic Asymmetric Synthesis, 2nd edn., ed. I. Ojima, VCH Publisher, New York, 2000, p. 281;
5. (c) T. Katsuki and V. S. Martin, Org. React., 1996, 48, 1;
6. (d) T. Katsuki, in Transition Metals for Organic Synthesis, eds. M. Beller and C. Bolm, VCH-Wiley, Weinheim, 1998, vol. 2, p. 261.
7. (a) A. S. Rao, in Comprehensive Organic Synthesis, eds. B. M. Trost and I. Fleming, Pergamon Press, Oxford, 1991, vol. 7, p. 357;
8. (b) V. Schurig and F. Betschinger, Chem. Rev., 1992, 92, 873;
9. (c) E. N. Jacobsen, in Catalytic Asymmetric Synthesis, ed. I. Ojima, VCH, New York, 1993, p. 159;
10. (d) P. Besse and H. Veschambre, Tetrahedron, 1994, 50, 8885;
11. (e) S. Pedragosa-Moreau, A. Archelas and R. Furstoss, Bull. Soc. Chim. Fr., 1995, 132, 769;
12. (f) T. Katsuki, Coord. Chem. Rev., 1995, 140, 189;
13. (g) T. Katsuki, J. Mol. Catal., 1996, 113, 87;
14. (h) C. T. Dalton, K. M. Ryan, V. M. Wall, C. Bousquet and D. G. Gilheany, Top. Catal., 1998, 5, 75;
15. (i) K. Muñiz-Fernández and C. Bolm, in Transition Metals for Organic Synthesis, eds. M. Beller and C. Bolm, VCH-Wiley, Weinheim, 1998, vol. 2, p. 271;
16. (j) T. Katsuki, in Comprehensive Asymmetric Catalysis, eds. E. N. Jacobsen, A. Pfaltz and H. Yamamoto, Springer, Berlin, 1999, vol. 2, p. 621;
17. (k) A. Archelas and R. Furstoss, Top. Curr. Chem., 1999, 200, 159;
18. (l) Y. N. Ito and T. Katsuki, Bull. Chem. Soc. Jpn., 1999, 72, 603;
19. (m) T. Flessner and S. Doye, J. Prakt. Chem., 1999, 341, 436;
20. (n) T. Katsuki, Adv. Synth. Catal., 2002, 344, 131.
21. Selected examples: (a) K. B. Sharpless and R. C. Michaelson, J. Am. Chem. Soc., 1973, 95, 6136; (b) R. Curci, F. Di Furia, R. Testi and G. Modena, J. Chem. Soc., Perkin Trans. 2, 1974, 752; (c) E. S. Gould, R. R. Hiatt and K. C. Irwin, J. Am. Chem. Soc., 1968, 90, 4573; (d) H. Glas, E. Herdtweck, G. R. J. Artus and W. R. Thiel, Inorg. Chem., 1998, 37, 3644; (e) C. Bolm, T. K. K. Luong and K. Harms, Chem. Ber./Recueil, 1997, 130, 887.
22. Selected examples: (a) K. B. Sharpless and R. C. Michaelson, J. Am. Chem. Soc., 1973, 95, 6136; (b) R. Curci, F. Di Furia, R. Testi and G. Modena, J. Chem. Soc., Perkin Trans. 2, 1974, 752; (c) E. S. Gould, R. R. Hiatt and K. C. Irwin, J. Am. Chem. Soc., 1968, 90, 4573; (d) H. Glas, E. Herdtweck, G. R. J. Artus and W. R. Thiel, Inorg. Chem., 1998, 37, 3644; (e) C. Bolm, T. K. K. Luong and K. Harms, Chem. Ber./Recueil, 1997, 130, 887.
23. Selected examples: (a) K. B. Sharpless and R. C. Michaelson, J. Am. Chem. Soc., 1973, 95, 6136; (b) R. Curci, F. Di Furia, R. Testi and G. Modena, J. Chem. Soc., Perkin Trans. 2, 1974, 752; (c) E. S. Gould, R. R. Hiatt and K. C. Irwin, J. Am. Chem. Soc., 1968, 90, 4573; (d) H. Glas, E. Herdtweck, G. R. J. Artus and W. R. Thiel, Inorg. Chem., 1998, 37, 3644; (e) C. Bolm, T. K. K. Luong and K. Harms, Chem. Ber./Recueil, 1997, 130, 887.
24. Selected examples: (a) K. B. Sharpless and R. C. Michaelson, J. Am. Chem. Soc., 1973, 95, 6136; (b) R. Curci, F. Di Furia, R. Testi and G. Modena, J. Chem. Soc., Perkin Trans. 2, 1974, 752; (c) E. S. Gould, R. R. Hiatt and K. C. Irwin, J. Am. Chem. Soc., 1968, 90, 4573; (d) H. Glas, E. Herdtweck, G. R. J. Artus and W. R. Thiel, Inorg. Chem., 1998, 37, 3644; (e) C. Bolm, T. K. K. Luong and K. Harms, Chem. Ber./Recueil, 1997, 130, 887.
25. Selected examples: (a) K. B. Sharpless and R. C. Michaelson, J. Am. Chem. Soc., 1973, 95, 6136; (b) R. Curci, F. Di Furia, R. Testi and G. Modena, J. Chem. Soc., Perkin Trans. 2, 1974, 752; (c) E. S. Gould, R. R. Hiatt and K. C. Irwin, J. Am. Chem. Soc., 1968, 90, 4573; (d) H. Glas, E. Herdtweck, G. R. J. Artus and W. R. Thiel, Inorg. Chem., 1998, 37, 3644; (e) C. Bolm, T. K. K. Luong and K. Harms, Chem. Ber./Recueil, 1997, 130, 887.
26. (a) H. Mimoun, M. Mignard, P. Brechot and L. Saussine, J. Am. Chem. Soc., 1986, 108, 3711;
27. (b) H. Mimoun, Catal. Today, 1987, 1, 281;
28. (c) H. Mimoun, P. Chaumette, M. Mignard, L. Saussine, J. Fischer and R. Weiss, Nouv. J. Chim., 1983, 7, 467.
29. (a) A. Butler, M. J. Clague and G. E. Meister, Chem. Rev., 1994, 94, 625;
30. (b) V. Conte, F. Di Furia and G. Licini, Appl. Catal. A: Gen., 1997, 157, 335;
31. (c) C. Bolm, Coord. Chem. Rev., in press.
32. (a) R. C. Michaelson, R. E. Palermo and K. B. Sharpless, J. Am. Chem. Soc., 1977, 99, 1990;
33. (b) K. B. Sharpless and T. R. Verhoeven, Aldrichim. Acta, 1979, 12, 63.
34. (a) N. Murase, Y. Hoshino, M. Oishi and H. Yamamoto, J. Org. Chem., 1999, 64, 338;
35. (b) Y. Hoshino, N. Murase, M. Oishi and H. Yamamoto, Bull. Chem. Soc. Jpn., 2000, 73, 1653;
36. (c) Y. Hoshino and H. Yamamoto, J. Am. Chem. Soc., 2000, 122, 10452;
37. (d) B. Traber, Y.-G. Jung, T. K. Park and J.-I. Hong, Bull. Korean Chem. Soc., 2001, 22, 547;
38. (e) H.-L. Wu and B.-J. Uang, Poster 74 at the Third International Symposium on Chemistry and Biological Chemistry of Vanadium, Osaka, Japan, November 26-29, 2001;
39. (f) C. Bolm and T. Kühn, Isr. J. Chem., 2001, 41, 263.
40. (a) C. Bolm and T. Kühn, Synlett, 2000, 899;
41. (b) C. Bolm, O. Beckmann, T. Kühn, C. Palazzi, W. Adam, P. Bheema Rao and C. R. Saha-Möller, Tetrahedron: Asymmetry, 2001, 12, 2441.
42. D. E. Babushkin and E. P. Talsi, React. Kinet. Catal. Lett., 2000, 71, 115.
43. O. W. Howarth, Progr. Nucl. Magn. Reson. Spectrosc., 1991, 22, 453.
44. (a) R. A. Sheldon and J. Dakka, Catal. Today, 1994, 19, 215;
45. (b) H. E. B. Lempers, A. Ripollès i Garcia and R. A. Sheldon, J. Org. Chem., 1998, 63, 1408.
46. (a) M. Postel, C. Brevard, H. Arzoumanian and J. G. Riess, J. Am. Chem. Soc., 1983, 105, 4922;
47. (b) A. T. Harrison and O. W. Howarth, J. Chem. Soc., Dalton Trans., 1985, 1173;
48. (c) W. J. Ray, Jr., D. C. Crans, J. Zheng, J. W. Burgner II, H. Deng and M. Mahroof-Tahir, J. Am. Chem. Soc., 1995, 117, 6015.
49. E. P. Talsi, V. D. Chinakov, V. P. Babenko and K. I. Zamaraev, J. Mol. Catal., 1993, 81, 235.
50. N. F. Orlov and M. G. Voronkov, Izv. Acad. Nauk SSSR Ser. Khim., 1959, 933.
51. (a) P. D. Bartlett and J. M. McBride, J. Am. Chem. Soc., 1965, 87, 1727;
52. (b) N. A. Milas and D. M. Surgenor, J. Am. Chem. Soc., 1946, 68, 205.