Amino acid-derived hydroxamic acids as chiral ligands in the vanadium catalysed epoxidation

Organic and Biomolecular Chemistry

Volumn 3, Issue 17, 2005, Pages 3194-3200

  Malkov, Andrei V ^a   Bourhani, Zaïnaba ^a   Kočovský, Pavel ^a  

^a UNIVERSITY OF GLASGOW   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOLS; CATALYSIS; NITROGEN COMPOUNDS; REACTION KINETICS; VANADIUM COMPOUNDS;

CHIRAL LIGANDS; ENANTIOSELECTIVITY; EPOXIDATION; HYDROXAMIC ACIDS;

AMINO ACIDS;

ALCOHOL DERIVATIVE; EPOXIDE; HYDROXAMIC ACID; LIGAND; ORGANOMETALLIC COMPOUND; SULFONAMIDE; VANADIUM;

ARTICLE; CATALYSIS; CHEMISTRY; CONFORMATION; STEREOISOMERISM; SYNTHESIS;

ALCOHOLS; CATALYSIS; EPOXY COMPOUNDS; HYDROXAMIC ACIDS; LIGANDS; MOLECULAR CONFORMATION; ORGANOMETALLIC COMPOUNDS; STEREOISOMERISM; SULFONAMIDES; VANADIUM;

EID: 25444523489     PISSN: 14770520     EISSN: None     Source Type: Journal    
DOI: 10.1039/b505324b     Document Type: Article

References (47)

1. For a review, see: B. Kurzak, H. Kozlowski and E. Farkas, Coord. Chem. Rev., 1992, 114, 169.
2. (a) For reviews, see: A. G. J. Ligtenbarg, R. Hage and B. L. Feringa, Coord. Chem. Rev., 2003, 237, 89;
3. (b) C. Bolm, Coord. Chem. Rev., 2003, 237, 245.
4. (a) For reviews, see: D. J. Berrisford, C. Bolm and K. B. Sharpless, Angew. Chem., Int. Ed., 1995, 34, 1059;
5. (b) T. Katsuki, in Comprehensive Asymmetric Catalysis, ed. E. N. Jacobsen, A. Pfaltz and H. Yamamoto, Springer-Verlag, Heidelberg, 1999; vol. 2, p. 621;
6. (c) T. Katsuki, Curr. Org. Chem., 2001, 5, 663;
7. (d) J. M. Keith, J. F. Larrow and E. N. Jacobsen, Adv. Synth. Catal., 2001, 343, 5;
8. (e) W. Adam, W. Malisch, K. J. Roschmann, C. R. Saha-Möller and W. A. Schenk, J. Organomet. Chem., 2002, 661, 3.
9. (a) T. Katsuki and K. B. Sharpless, J. Am. Chem. Soc:., 1980, 102, 5974;
10. (b) T. Katsuki and V. S. Martin, Org. React. (N. Y.), 1996, 48, 1.
11. (a) E. N. Jacobsen and M. H. Wu, in Comprehensive Asymmetric Catalysis, ed. E. N. Jacobsen, A. Pfaltz and H. Yamamoto, Springer-Verlag, Heidelberg, 1999; vol. 2, p. 649;
12. (b) T. Katsuki, Adv. Synth. Catal., 2002, 344, 131;
13. T. Katsuki, Synlett, 2003, 281.
14. (a) K. M. Ryan, C. Bousquet and D. G. Gilheany, Tetrahedron Lett., 1999, 40, 3616;
15. (b) P. Brandt, P.-O. Norrby, A. M. Daly and D. C. Gilheany, Chem. Eur. J., 2002, 8, 4299.
16. Y. Shi, Acc. Chem. Res., 2004, 37, 488.
17. (a) S. Yamada, T. Mashiko and S. Terashima, J. Am. Chem. Soc., 1977, 99, 1988;
18. (b) R. J. Cross, P. D. Newman, R. D. Peacock and D. Stirling, J. Mol. Catal. A., 1999, 144, 273.
19. R. C. Michaelson, R. E. Palermo and K. B. Sharpless, J. Am. Chem. Soc., 1977, 99, 1990.
20. K. B. Sharpless and T. R. Verhoeven, Aldrichimica Acta, 1979, 12, 63.
21. (a) N. Murase, Y. Hoshino, M. Oishi and H. Yamamoto, J. Org. Chem., 1999, 64, 338;
22. (b) Y. Hoshino, N. Murase, M. Oishi and H. Yamamoto, Bull. Chem. Soc. Jpn., 2000, 73, 1653.
23. (a) C. Bolm and T. Kühn, Synlett, 2000, 899;
24. (b) C. Bolm and T. Kühn, Isr. J. Chem., 2001, 41, 263;
25. C. Bolm, O. Beckmann, T. Kühn, C. Palazzi, W. Adam, P. B. Rao and C. R. Saha-Möller, Tetrahedron: Asymmetry, 2001, 12, 2441;
26. B. Traber, Y.-G. Jung, T. K. Park and J.-I. Hong, Bull. Korean Chem. Soc., 2001, 22, 547;
27. (e) H.-L. Wu and B.-J. Uang, Tetrahedron: Asymmetry, 2002, 13, 2625;
28. (f) W. Adam, A. K. Beck, A. Pichota, C. R. Saha-Möller, D. Seebach, N. Vogl and R. Zhang, Tetrahedron: Asymmetry, 2003, 14, 1355.
29. (a) K. P. Bryliakov, E. P. Talsi, C. Bolm and T. Kühn, New J. Chem., 2003, 27, 609;
30. (b) K. P. Bryliakov and E. P. Talsi, Kinet. Catal, 2003, 44, 334;
31. (c) K. P. Bryliakov, E. P. Talsi, S. N. Stas'ko, O. A. Kholdeeva, S. A. Popov and A. V. Tkachev, J. Mol. Catal. A, 2003, 194, 79.
32. (a) Y. Hoshino and H. Yamamoto, J. Am. Chem. Soc., 2000, 122, 10452.
33. For a related epoxidation of homoallylic alcohols, see:; N. Makita, Y. Hoshino and H. Yamamoto, Angew. Chem., Int. Ed., 2003, 42, 941.
34. P. J. Walsh, Acc. Chem. Res., 2003, 36, 739.
35. For example, replacing the benzhydryl hydroxylamine moiety in ligand 7a with phenylhydroxylamine resulted in a dramatic loss of selectivity in the model reactions, giving nearly racemic products.
36. The use of acid chlorides is dictated by the lowjeactivity of the nitrogen of hydroxylamines. With less reactive acylating agents, such as mixed anhydrides, the competing O-acylation predominates.
37. H. Tokuyama, T. Kuboyama, A. Amano, T. Yamashita and T. Fukuyama, Synthesis, 2000, 1299.
38. R. Salas-Coronado, A. Vasques-Badillo, M. Medina-Garcia, J. G. Garcia-Colon, H. Nöth, R. Contreras and A. Flores-Parra, J. Mol. Struct. (Theochem), 2001, 543, 259.
39. (a) A. V. Malkov, J. B. Hand and P. Kočovský, Chem. Commun., 2003, 1948;
40. (b) A. V. Malkov, A. Mariani, K. MacDougall and P. Kočovský , Org. Lett., 2004, 6, 2253.
41. A. M. Gonzales-Cameno, D. Badia, E. Dominguez, M. K. Urtiaga, M. I. Arriortua and X. Solans, Tetrahedron, 1994, 50, 10971.
42. Y. Gao, R. M. Hanson, J. M. Klunder, S. Y. Ko, H. Masamune and K. B. Sharpless, J. Am. Chem. Soc., 1987, 109, 5765.
43. S. E. Denmark, D. C. Forbes, D. S. Hays, J. DePue and R. G. Wilde, J. Org. Chem., 1995, 60, 1391.
44. E. Medina, A. Moyano, M. Pericas and A. Riera, Helv. Chim. Acta, 2000, 83, 972.
45. A. Vidal-Ferran, E. Medina, A. Moyano, M. Pericas and A. Riera, Tetrahedron: Asymmetry, 1997, 8, 1581.
46. R. Martin, G. Islas, A. Moyano, M. A. Pericàs and A. Riera, Tetrahedron, 2001, 57, 6367.
47. H. E. Zimmerman, L. Singer and B. S. Thyagarajan, J. Am. Chem. Soc., 1959, 81, 108.