The RuO4-catalysed dihydroxylation, ketohydroxylation and mono oxidation - Novel oxidation reactions for the synthesis of diols and α-hydroxy ketones

Organic and Biomolecular Chemistry

Volumn 2, Issue 17, 2004, Pages 2403-2407

  Plietker, Bernd ^a   Niggemann, Meike ^a  

^a TU DORTMUND UNIVERSITY   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

CATALYSIS; CHEMICAL BONDS; COORDINATION REACTIONS; OLEFINS; OXIDATION; RUTHENIUM COMPOUNDS; STEREOCHEMISTRY; SYNTHESIS (CHEMICAL);

MOLECULAR ARCHITECTURES; NATURAL PRODUCTS; OXIDANTS; REGIOSELECTIVITY;

KETONES;

GLYCOL; KETONE; RUTHENIUM DERIVATIVE; RUTHENIUM TETROXIDE;

CATALYSIS; CHEMISTRY; CONFORMATION; HYDROXYLATION; OXIDATION REDUCTION REACTION; REVIEW; SYNTHESIS;

CATALYSIS; GLYCOLS; HYDROXYLATION; KETONES; MOLECULAR CONFORMATION; OXIDATION-REDUCTION; RUTHENIUM COMPOUNDS;

EID: 4744339944     PISSN: 14770520     EISSN: None     Source Type: Journal    
DOI: 10.1039/b407937j     Document Type: Article

References (45)

1. Comprehensive Asymmetric Catalysis I-III, ed. E. N. Jacobsen, A. Pfaltz and H. Yamamoto, Springer-Verlag, Berlin, Heidelberg, New York, 1999.
2. B. M. Trost, Science, 1991, 254, 1471.
3. Houben-Weyl, Stereoselective Synthesis, ed. G. Helmchen, R. W. Hoffmann, J. Mulzer and E. Schaumann, Thieme-Verlag, Stuttgart, New York, 1996, vol. 8, p. 4497.
4. nd edn., ed. I. Ojima, Wiley-VCH, New York-Weinheim, 2000, p. 357;
5. nd edn., ed. I. Ojima, Wiley-VCH, New York-Weinheim, 2000, p. 399.
6. G. C. Fu in Transition Metals for Organic Synthesis, ed. M. Beller and C. Bolm, Wiley-VCH, Weinheim-New York, 1998, vol. 2, pp. 141.
7. (a) T. Katsuki in Transition Metals for Organic Synthesis, ed. M. Beller and C. Bolm, Wiley-VCH, Weinheim-New York, 1998, vol. 2, pp. 261;
8. (b) K. Muniz-Fernandez and C. Bolm in Transition Metals for Organic Synthesis, ed. M. Beller and C. Bolm, Wiley-VCH, Weinheim-New York, 1998, vol. 2, pp. 272;
9. (c) R. W. Fischer, W. A. Herrmann and T. Weskamp in Transition Metals for Organic Synthesis, ed. M. Beller and C. Bolm, Wiley-VCH, Weinheim-New York, 1998, vol. 2, pp. 282;
10. (d) W. R. Thiel in Transition Metals for Organic Synthesis, ed. M. Beller and C. Bolm, Wiley-VCH, Weinheim-New York, 1998, vol. 2, pp. 290;
11. (e) R. L. Halterman in Transition Metals for Organic Synthesis, ed. M. Beller and C. Bolm, Wiley-VCH, Weinheim-New York, 1998, vol. 2, pp. 300.
12. nd edn., ed. I. Ojima, Wiley-VCH, New York-Weinheim, 2000, p. 357;
13. nd edn., ed. I. Ojima, Wiley-VCH, New York-Weinheim, 2000, p. 399.
14. (a) S.-I. Murahashi and N. Komiya in Biomimetic Oxidations Catalyzed by Transition Metal Complexes, ed. B. Meunier, Imperial College Press, London, 2000, pp. 563;
15. (b) S.-I. Murahashi, Pure Appl. Chem., 1992, 64, 403;
16. (c) ruthenium-catalysed: S.-I. Murahashi, T. Saito, H. Hanaoka, Y. Murakami, T. Naota, H. Kumobayashi and S. Akutagawa, J. Org. Chem., 1993, 58, 2929;
17. (d) osmium-catalysed: S.-I. Murahashi, T. Naota and H. Hanaoka, Chem. Lett., 1993, 1767;
18. 4-Ni-catalysed: T. Takai, T. Yamada and T. Mukaiyama, Chem. Lett., 1991, 1499;
19. 4-assisted: S. Baskaran, J. Das and S. Chandrasekaran, J. Org. Chem., 1989, 54, 5182.
20. (a) B. Plietker and M. Niggemann, Org. Lett., 2003, 5, 3353;
21. (b) B. Plietker, M. Niggemann and A. Pollrich, Org. Biomol. Chem., 2004, 2, 1116.
22. (a) B. Plietker, J. Org. Chem., 2003, 68, 7123;
23. (b) B. Plietker, 2004, manuscript submitted for publication.
24. B. Plietker, Org. Lett., 2004, 6, 289.
25. (a) T. K. M. Shing, V. W.-F. Tai and E. K. W. Tam, Angew. Chem., 1994, 106, 2408; T. K. M. Shing, V. W.-F. Tai and E. K. W. Tarn, Angew. Chem., Int. Ed. Engl., 1994, 33, 2312;
26. (a) T. K. M. Shing, V. W.-F. Tai and E. K. W. Tam, Angew. Chem., 1994, 106, 2408; T. K. M. Shing, V. W.-F. Tai and E. K. W. Tarn, Angew. Chem., Int. Ed. Engl., 1994, 33, 2312;
27. (b) T. K. M. Shing, E. K. W. Tam, V. W. F. Tai, I. H. F. Chung and Q. Jiang, Chem. Eur. J., 1996, 2, 50;
28. (c) T. K. M. Shing and E. K. W. Tam, Tetrahedron Lett., 1999, 40, 2179.
29. (a) J. Frunzke, C. Loschen and G. Frenking, J. Am. Chem. Soc., 2004, 126, 3642;
30. 3 has been used recently for the oxidative cleavage of olefins: D. Yang and C. Zhang, J. Org. Chem., 2001, 5, 3353.
31. (a) J. K. Cha, W. J. Christ and Y. Kishi, Tetrahedron, 1984, 40, 2247;
32. (b) J. K. Cha and N.-S. Kim, Chem. Rev., 1995, 95, 1761.
33. 4/Oxone has been used recently for the oxidative cleavage of olefins: B. R. Travis, R. S. Narayan and B. Borhan, J. Am. Chem. Soc., 2002, 124, 3824.
34. (a) D. Enders and U. Kallfass, Angew. Chem., 2002, 114, 1822; D. Enders and U. Kallfass, Angew. Chem., Int. Ed., 2002, 41, 1743;
35. (a) D. Enders and U. Kallfass, Angew. Chem., 2002, 114, 1822; D. Enders and U. Kallfass, Angew. Chem., Int. Ed., 2002, 41, 1743;
36. (b) P. Dünkelmann, D. Kolter-Jung, A. Nitsche, A. S. Demir, P. Siegert, B. Lingen, M. Baumann, M. Pohl and M. Müller, J. Am. Chem. Soc., 2002, 124, 12084;
37. (c) A. S. Demir, O. Sesenoglu, E. Eren, B. Hosrik, M. Pohl, E. Janzen, D. Kolter, R. Feldmann, P. Duenkelmann and M. Müller, Adv. Synth. Catal., 2002, 1, 96 (and references cited therein).
38. K. Morikawa, J. Park, P. G. Andersson, T. Hashiyama and K. B. Sharpless, J. Am. Chem. Soc., 1993, 115, 8463.
39. (a) S. P. Brown, M. P. Brochu, C. J. Sinz and D. W. MacMillan, J. Am. Chem. Soc., 2003, 125, 10808;
40. (b) G. Zhoung, Angew. Chem., 2003, 115, 4379; G. Zhoung, Angew. Chem., Int. Ed., 2003, 42, 4247;
41. (b) G. Zhoung, Angew. Chem., 2003, 115, 4379; G. Zhoung, Angew. Chem., Int. Ed., 2003, 42, 4247;
42. (c) A. Bogevig, H. Sundén and A. Córdova, Angew. Chem., 2004, 116, 1129; A. Bogevig, H. Sundén and A. Córdova, Angew. Chem., Int. Ed., 2004, 43, 1109;
43. (c) A. Bogevig, H. Sundén and A. Córdova, Angew. Chem., 2004, 116, 1129; A. Bogevig, H. Sundén and A. Córdova, Angew. Chem., Int. Ed., 2004, 43, 1109;
44. (d) Y. Hayashi, J. Yamaguchi, T. Sumiya and M. Shoji, Angew. Chem., 2004, 116, 1132; Y. Hayashi, J. Yamaguchi, T. Sumiya and M. Shoji, Angew. Chem., Int. Ed., 2004, 43, 1112.
45. (d) Y. Hayashi, J. Yamaguchi, T. Sumiya and M. Shoji, Angew. Chem., 2004, 116, 1132; Y. Hayashi, J. Yamaguchi, T. Sumiya and M. Shoji, Angew. Chem., Int. Ed., 2004, 43, 1112.