The RuO4-catalyzed ketohydroxylation. Part 1. Development, scope, and limitation

Journal of Organic Chemistry

Volumn 69, Issue 24, 2004, Pages 8287-8296

  Plietker, Bernd ^a  

^a TU DORTMUND UNIVERSITY   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

CATALYSIS; CHEMICAL BONDS; KETONES; OLEFINS; OXIDATION; PRECIPITATION (CHEMICAL); RUTHENIUM COMPOUNDS; STOICHIOMETRY; SUBSTRATES;

ACYLOINS; KETOHYDROXYLATION; OXONE; REGIOSELECTIVITY;

HYDROXYLATION;

KETONE DERIVATIVE; RUTHENIUM DERIVATIVE; ALKENE; KETONE; ORGANOMETALLIC COMPOUND; RUTHENIUM TETROXIDE;

ARTICLE; CATALYSIS; CHEMICAL BOND; CHEMICAL REACTION; HYDROXYLATION; MODEL; OXIDATION; STOICHIOMETRY; SYNTHESIS; TEMPERATURE DEPENDENCE; CHEMICAL STRUCTURE; CHEMISTRY; OXIDATION REDUCTION REACTION; STEREOISOMERISM;

ALKENES; CATALYSIS; HYDROXYLATION; KETONES; MOLECULAR STRUCTURE; ORGANOMETALLIC COMPOUNDS; OXIDATION-REDUCTION; RUTHENIUM COMPOUNDS; STEREOISOMERISM;

EID: 9344260283     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo048822s     Document Type: Article

References (73)

1. (a) Kobayashi, J.; Kubota, T.; Endo, T.; Tsuda, M. J. Org. Chem. 2001, 66, 134.
2. (b) Tsuda, M.; Endo, T.; Kobayashi, J. J. Org. Chem. 2000, 65, 1349.
3. (c) Kubota, T.; Endo, T.; Tsuda, M.; Shiro, M.; Kobayashi, J. Tetrahedron 2001, 57, 6175.
4. (d) For a current review on amphidinolides, see: Chakraborty, T. K.; Das, D.; Curr. Med. Chem.: Anti-Cancer Agents 2001, 1, 131.
5. (a) Enders, D.; Kallfass, U. Angew. Chem. 2002, 114, 1822; Angew. Chem., Int. Ed. 2002, 41, 1743.
6. (a) Enders, D.; Kallfass, U. Angew. Chem. 2002, 114, 1822; Angew. Chem., Int. Ed. 2002, 41, 1743.
7. (b) Dünkelmann, P.; Kolter-Jung, D.; Nitsche, A.; Demir, A. S.; Siegert, P.; Lingen, B.; Baumann, M.; Pohl, M.; Müller, M. J. Am. Chem. Soc. 2002, 124, 12084.
8. (c) Demir, A. S.; Sesenoglu, O.; Eren, E.; Hosrik, B.; Pohl, M.; Janzen, E.; Kolter, D.; Feldmann, R.; Duenkelmann, P.; Müller, M. Adv. Synth. Catal. 2002, 1, 96 (and references therein).
9. Zhou, P.; Chen, B. A.; Davies, F. A. In Asymmetric Oxidation Reactions; Katsuki, T., Ed.; Oxford University Press: Oxford, 2001; p 128.
10. Morikawa, K.; Park, J.; Andersson, P. G.; Hashiyama, T.; Sharpless, K. B. J. Am. Chem. Soc. 1993, 115, 8463.
11. (a) Brown, S. P.; Brochu, M. P.; Sinz, C. J.; MacMillan, D. W. J. Am. Chem. Soc. 2003, 125, 10808.
12. (b) Zhoung, G. Angew. Chem. 2003, 115, 4379; Angew. Chem., Int. Ed. 2003, 42, 4247.
13. (b) Zhoung, G. Angew. Chem. 2003, 115, 4379; Angew. Chem., Int. Ed. 2003, 42, 4247.
14. (c) Bogevig, A.; Sundén, H.; Córdova, A. Angew. Chem. 2004, 116, 1129; Angew. Chem., Int. Ed. 2004, 43, 1109.
15. (c) Bogevig, A.; Sundén, H.; Córdova, A. Angew. Chem. 2004, 116, 1129; Angew. Chem., Int. Ed. 2004, 43, 1109.
16. (d) Hayashi, Y.; Yamaguchi, J.; Sumiya, T.; Shoji, M. Angew. Chem. 2004, 116, 1132; Angew. Chem., Int. Ed. 2004, 43, 1112.
17. (d) Hayashi, Y.; Yamaguchi, J.; Sumiya, T.; Shoji, M. Angew. Chem. 2004, 116, 1132; Angew. Chem., Int. Ed. 2004, 43, 1112.
18. (a) Connon, S. J.; Blechert, S. Angew. Chem., Int. Ed. 2003, 42, 1900.
19. (b) Fürstner, A. Adv. Synth. Catal. 2002, 344, 567.
20. (c) Trnka, T. M.; Grubbs, R. H. Acc. Chem. Res. 2001, 34, 18.
21. (d) Schrock, R. R. In Topics in Organometallic Chemistry 1 - Alkene Metathesis in Organic Synthesis; Fürstner, A., Ed.; Springer-Verlag: Berlin, Heidelberg, 1998; p 1.
22. (e) Fürstner, A. In Topics in Organometallic Chemistry 1 - Alkene Metathesis in Organic Synthesis; Fürstner, A., Ed.; Springer-Verlag: Berlin, Heidelberg, 1998; p 37.
23. (f). Nicolaou, K. C.; King, N. P.; He, Y. In Topics in Organometallic Chemistry 1 - Alkene Metathesis in Organic Synthesis; Fürstner, A., Ed.; Springer-Verlag: Berlin, Heidelberg, 1998; p 73.
24. (a) Johnson, R. A.; Sharpless, K. B. In Catalytic Asymmetric Synthesis, 2nd ed.; Ojima, I., Ed.; Wiley-VCH: New York, Weinheim, 2000; p 357.
25. (b) Bolm, C.; Hildebrand, J. P.; Muniz K. In Catalytic Asymmetric Synthesis, 2nd ed.; Ojima, I., Ed.; Wiley-VCH: New York, Weinheim, 2000; p 399.
26. Acyloins are byproducts in dihydroxylation processes. (a) In osmium-catalyzed oxidations, see ref 14a.
27. (b) In ruthenium-catalyzed oxidations: Zimmer, R.; Homann, K.; Angermann, J.; Reissig, H.-U. Synthesis 1999, 1223.
28. (c) In manganese-mediated oxidations: Carlson, R. G.; Pierce, J. K. J. Org. Chem. 1971, 36, 2319.
29. Enantiomerically enriched acyloins can be obtained via mono-oxidation of enantiomerically enriched vic-diols: (a) D'Accolti, L.; Detomaso, A.; Fusco, C.; Rosa, A.; Curci, R. J. Org. Chem. 1993, 58, 3600.
30. (b) Curci, R.; D'Accolti, L.; Dinoi, A.; Fusco, C.; Rosa, A. Tetrahedron Lett. 1996, 37, 115.
31. (c) For a catalytic version of this reaction, see: Plietker, B. Org. Lett. 2004, 6, 289.
32. (d) The desymmetrisation of meso-diols has been described: Adam, W.; Saha-Möller, C. R.; Zhao, C.-G. J. Org. Chem. 1999, 64, 7492 (and references therein).
33. Fleming, S. A.; Carroll, S. M.; Hirschi, J.; Liu, R.; Pace, J. L.; Redd, J. T. Tetrahedron Lett. 2004, 45, 3341.
34. For direct conversions of olefins to α-ketols see: (a) Murahashi, S.-I.; Komiya, N. In Biomimetic Oxidations Catalyzed by Transition Metal Complexes; Meunier, B, Ed.; Imperial College Press: London, 2000; p 563.
35. (b) Murahashi, S.-I. Pure Appl. Chem. 1992, 64, 403.
36. (c) Ruthenium-catalyzed: Murahashi, S.-I.; Saito, T.; Hanaoka, H.; Murakami, Y.; Naota, T.; Kumobayashi, H.; Akutagawa, S. J. Org. Chem. 1993, 58, 2929.
37. (d) Osmium-catalyzed: Murahashi, S.-I.; Naota, T.; Hanaoka, H.; Chem. Lett. 1993, 1767.
38. 4-Ni-catalyzed: Takai, T.; Yamada, T.; Mukaiyama, T. Chem. Lett. 1991, 1499.
39. 4-assisted: Baskaran, S.; Das, J.; Chandrasekaran, S. J. Org. Chem. 1989, 54, 5182.
40. (a) Plietker, B.; Niggemann, M. Org. Lett. 2003, 5, 3353.
41. (b) Plietker, B.; Niggemann, M.; Pollrich, A. Org. Biomol. Chem. 2004, 2, 1116.
42. Plietker, B. J. Org. Chem. 2003, 68, 7123.
43. Frunzke, J.; Loschen, C.; Frenking, G. J. Am. Chem. Soc. 2004, 126, 3642.
44. (a) Becker, H.; Sharpless, K. B. In Asymmetric Oxidation Reactions; Katsuki, T., Ed.; Oxford University Press: New York, 2001; p 81.
45. (b) Morikawa, K.; Park, J.; Andersson, P. G.; Hashiyama, T.; Sharpless, K. B. J. Am. Chem. Soc. 1993, 115, 8463.
46. (a) Sharpless, K. B.; Akashi, K. J. Am. Chem. Soc. 1976, 98, 1986.
47. (b) Akashi, K.; Palermo, R. E.; Sharpless, K. B. J. Org. Chem. 1978, 43, 2063.
48. Sharpless, K. B.; Amberg, W.; Bennani, Y. L.; Crsipino, G. A.; Hartung, J.; Jeong, K.-S.; Kwong, H.-L.; Morikawa, K.; Wang, Z.-M.; Xu, D.; Zhang, X.-L. J. Org. Chem. 1992, 57, 2768.
49. Similar observations were published by Sharpless for osmium-catalyzed dihydroxylation: Dupau, P.; Epple, R.; Thomas, A. A.; Fokin, V. V.; Sharpless, K. B. Adv. Synth. Catal. 2002, 344, 421.
50. Yang, D.; Zhang, C. J. Org. Chem. 2001, 5, 3353;
51. Ley, S. V.; Norman, J.; Griffith, W. P.; Marsden, S. P. Synthesis 1994, 639.
52. Sliwa, W. Trans. Met. Chem. 1989, 14, 321.
53. 4 catalyzes efficiently the cleavage of vic-diols: see ref 12b.
54. (a) Cha, J. K.; Christ, W. J.; Kishi, Y. Tetrahedron 1984, 40, 2247.
55. (b) Cha, J. K.; Kim, N.-S. Chem. Rev. 1995, 95, 1761.
56. Sarkar, A.; Yemul, O. S.; Bandgar, B. P.; Gaikwad, N. B.; Prakash, P. P. Org. Prep. Proced. Int. 1996, 28, 613.
57. Persson, E. S. M.; Bäckvall, J.-E. Acta Chem. Scand. 1995, 49, 899.
58. Denmark, S. E.; Edwards, J. P. J. Org. Chem. 1991, 56, 6974.
59. Hurd, C. D.; Schmerling, L. J. Am. Chem. Soc. 1937, 59, 107.
60. Manhart, E.; von Werner, K. Synthesis 1978, 705.
61. Gensler, W. J.; Rockett, J. C. J. Am. Chem. Soc. 1955, 77, 3262.
62. Pyne, S. G.; David, D. M.; Dong, Z. Tetrahedron Lett. 1998, 39, 8499.
63. Ueyama, N.; Kamabuchi, K.; Nakamura, A. J. Chem. Soc., Dalton Trans. 1985, 635.
64. Srinivasan, N. S.; Lee, D. G. Synthesis 1979, 520.
65. Tamura, Y.; Yakura, T.; Haruta, J.-I.; Kita, Y. Tetrahedron Lett. 1985, 26, 3837.
66. Craig, D.; Daniels, K.; MacKenzie, A. R. Tetrahedron 1993, 49, 11263.
67. Bovicelli, P.; Sanetti, A.; Lupatelli, P. Tetrahedron 1996, 52, 10969.
68. Blatt, K.; Hawkins, W. L. J. Am. Chem. Soc. 1936, 58, 81.
69. Shing, T. K. M.; Tam, E. K. W.; Tai, V. W. F.; Chung, I. H. F.; Jiang, Q. Chem. Eur. J. 1996, 2, 50.
70. El-Qisairi, A. K.; Qaseer, H. A. J. Organomet. Chem. 2002, 659 (1-2), 50.
71. Matsubara, S.; Takai, K.; Nozaki, H. Bull. Chem. Soc. Jpn. 1983, 56, 2029.
72. Crout, D. H. G.; Rathbone, D. L. Synthesis 1989, 40.
73. Su, G.; Dorizon, P.; Ollivier, J. J. Salaun, Synth. Commun. 1998, 28, 1351.