MTO and OsO4: An efficient catalytic couple for mild H2O2-based asymmetric dihydroxylation of olefins

Chemistry - A European Journal

Volumn 9, Issue 12, 2003, Pages 2783-2788

  Jonsson, Sandra Y ^a   Adolfsson, Hans ^a   Bäckvall, Jan E ^a  

^a STOCKHOLM UNIVERSITY   (Sweden)

Author keywords

Asymmetric catalysis; Dihydroxylation; Hydrogen peroxide; Osmium; Rhenium

Indexed keywords

AMINES; CATALYSIS; OSMIUM COMPOUNDS; OXIDATION;

ELECTRON TRANSFER MEDIATORS (ETM);

OLEFINS;

ALKENE DERIVATIVE; HYDROGEN PEROXIDE; METHYLTRIOXORHENIUM; OSMIUM; RHENIUM; UNCLASSIFIED DRUG;

AMINATION; ARTICLE; ASYMMETRIC SYNTHESIS; CATALYSIS; CHIRALITY; DIHYDROXYLATION; ELECTRON TRANSPORT; ENANTIOMER; LIGAND BINDING; OXIDATION; PRODUCT RECOVERY; RECYCLING;

EID: 0038790020     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/chem.200304828     Document Type: Article

References (65)

1. a) M. Schröder, Chem. Rev. 1980, 80, 187;
2. b) H. C. Kolb, M. S. VanNieuwenhze, K. B. Sharpless, Chem. Rev. 1994, 94, 2483;
3. c) H. C. Kolb, K. B. Sharpless in Transition Metals for Organic Synthesis, Vol. 2 (Eds.: M. Beller, C. Bolm), VCH Wiley, Weinheim, 1998;
4. d) M. Beller, K. B. Sharpless in Applied Homogeneous Catalysis (Eds.: B. Cornlis, W. A. Herrmann), VCH, Weinheim, 1996;
5. e) I. E. Marko, J. S. Svendsen in Comprehensive Asymmetric Catalysis II (Eds.: E. N. Jacobsen, A. Pfaltz, H. Yamamoto), Springer, Berlin, 1999;
6. f) C. Bolm, J. P. Hildebrand, K. Muniz in Catalytic Asymmetric Synthesis (Ed.: I. Ojima), Wiley-VCH, New York, 2000.
7. a) V. VanRheenen, R. C. Kelly, D. Y. Cha, Tetrahedron Lett. 1976, 1973;
8. b) V. VanRheenen, D. Y. Cha, W. M. Hartley, Org. Synth. Coll. Vol. VI 1988, 342.
9. E. N. Jacobsen, I. Markó, W. S. Mungall, G. Schröder, K. B. Sharpless, J. Am. Chem. Soc. 1988, 110, 1968.
10. M. Minato, K. Yamamoto, J. Tsuji, J. Org. Chem. 1990, 55, 766.
11. H.-L. Kwong, C. Sorato, Y. Ogino, H. Chen, K. B. Sharpless, Tetrahedron Lett. 1990, 31, 2999.
12. a) L. Ahrgren, L. Sutin, Org. Process Res. Dev. 1997, 1, 425;
13. b) C. Döbler, G. M. Mehltretter, U. Sundermaier, M. Beller, J. Organomet. Chem. 2001, 621, 70.
14. a) N. A. Milas, S. Sussman, J. Am. Chem. Soc. 1936, 58, 1302;
15. b) N. A. Milas, S. Sussman, J. Am. Chem. Soc. 1937, 59, 2345;
16. c) N. A. Milas, S. Sussman, H. S. Mason, J. Am. Chem. Soc. 1939, 61, 1844;
17. d) N. A. Milas, J. H. Trepagnier, J. T. Nolan, M. I. Iliopulos, J. Am. Chem. Soc. 1959, 81, 4730.
18. A. Krief, C. Colaux-Castillo, Tetrahedron Lett. 1999, 40, 4189.
19. a) C. Döbler, G. M. Mehltretter, M. Beller, Angew. Chem. 1999, 111, 3211; Angew. Chem. Int. Ed. 1999, 38, 3026;
20. a) C. Döbler, G. M. Mehltretter, M. Beller, Angew. Chem. 1999, 111, 3211; Angew. Chem. Int. Ed. 1999, 38, 3026;
21. b) C. Döbler, G. M. Mehltretter, U. Sundermeier, M. Beller, J. Am. Chem. Soc. 2000, 122, 10289.
22. a) K. Bergstad, S. Y. Jonsson, J.-E. Bäckvall, J. Am. Chem. Soc. 1999, 121, 10424;
23. b) S. Y. Jonsson, K. Färnegårdh, J.-E. Bäckvall, J. Am. Chem. Soc. 2001, 123, 1365.
24. K. Bergstad, J.-E. Bäckvall, J. Org. Chem. 1998, 63, 6650.
25. a) C. C. Moser, J. M. Keske, K. Warncke, R. S. Faird, P. L. Dutton, Nature 1992, 355, 796;
26. b) J. H. A. Nugent, Eur. J. Biochem. 1996, 237, 519;
27. c) M. N. Hughes, The Inorganic Chemistry of Biological Processes; Wiley, Chichester (UK), 1981.
28. a) J. Tsuji, Palladium Reagents and Catalysts. Innovations in Organic Synthesis Wiley, Chichester (UK), 1995;
29. b) J.-E. Bäckvall, R. B. Hopkins, H. Grennberg, M. Mader, A. K. Awasthi, J. Am. Chem. Soc. 1990, 112, 5160;
30. c) J. Wöltinger, J.-E. Bäckvall, A. Zsigmond, Chem. Eur. J. 1999, 5, 1460;
31. d) J.-E. Bäckvall, R. L. Chowdhury, U. Karlsson, J. Chem. Soc. Chem. Commun. 1991, 473;
32. e) G.-Z. Wang, U. Andreasson, J.-E. Bäckvall, J. Chem. Soc. Chem. Commun. 1994, 1037;
33. f) S. E. Byström, E. M. Larsson, B. Åkermark, J. Org. Chem. 1990, 55, 5674;
34. g) T. Yokota, Y. Sakurai, Y. Ishii, Tetrahedron Lett. 1997, 38, 3923;
35. h) S. Torii, P. Liu, N. Bhuvaneswari, C. Amatore, A. Jutand, J. Org. Chem. 1996, 61, 3055.
36. A. H. Éll, S. Y. Jonsson, A. Börje, H. Adolfsson, J.-E. Bäckvall, Tetrahedron Lett. 2001, 42, 2569.
37. K. B. Sharpless, W. Amberg, Y. L. Bennani, G. A. Crispino, J. Hartung; K.-S. Jeong, H.-L. Kwong, K. Morikowa, Z.-M. Wang, D. Xu, X.-L. Zhang, J. Org. Chem. 1992, 57, 2768.
38. S. Y. Jonsson, H. Adolfsson, J.-E. Bäckvall, Org. Lett. 2001, 3, 3463.
39. a) W. A. Herrmann, R. W. Fischer, D. W. Marz, Angew. Chem. 1991, 103, 1706; Angew. Chem. Int. Ed. Engl. 1991, 30, 1638;
40. a) W. A. Herrmann, R. W. Fischer, D. W. Marz, Angew. Chem. 1991, 103, 1706; Angew. Chem. Int. Ed. Engl. 1991, 30, 1638;
41. b) J. Rudolph, K. L. Reddy, J. P. Chiang, K. B. Sharpless, J. Am. Chem. Soc. 1997, 119, 6189;
42. c) C. Copéret, H. Adolfsson, K. B. Sharpless, Chem. Commun. 1997, 1565;
43. d) A. M. Al-Ajlouni, J. H. Espenson, J. Am. Chem. Soc. 1995, 117, 9243;
44. e) P. Gisdakis, S. Antonczak, S. Köstlmeier, W. A. Herrmann, N. Rösch, Angew. Chem. 1998, 110, 1638; Angew. Chem. Int. Ed. 1998, 37, 2211.
45. e) P. Gisdakis, S. Antonczak, S. Köstlmeier, W. A. Herrmann, N. Rösch, Angew. Chem. 1998, 110, 1638; Angew. Chem. Int. Ed. 1998, 37, 2211.
46. a) G. Strukul, Catalytic Oxidations with Hydrogen Peroxide as Oxidant, Kluwer, Dordrecht (The Netherlands), 1992;
47. b) G. Venturello, E. Alneri, M. Ricci, J. Org. Chem. 1983, 48, 3831;
48. c) K. Sato, M. Aoki, M. Ogawa, T. Hashimoto, R. Noyori, J. Org. Chem. 1996, 61, 8310;
49. d) D. E. DeVos, P. A. Jacobs, Tetrahedron Lett. 1998, 39, 3221;
50. e) M. C. White, A. G. Doyle, E. N. Jacobsen, J. Am. Chem. Soc. 2001, 123, 7194.
51. V. Conte, F. Di Furia, G. Licini, Appl. Catal. A Gen. 1997. 157, 335.
52. M. N. Sheng, G. Zajacek, J. Org. Chem. 1968, 33, 588.
53. J. H. Espenson, Chem. Commun. 1999, 479.
54. a) H. Adolfsson, C. Copéret, J. P. Chiang, A. K. Yudin, J. Org. Chem. 2000, 65, 8651;
55. b) H. Adolfsson, A. Converso, K. B. Sharpless, Tetrahedron Lett. 1999, 40, 3991.
56. a) R. W. Murray, K. Iyanar, J. Chen, J. T. Wearing, Tetrahedron Lett. 1995, 36, 6415;
57. b) Z. Zhu, J. H. Espenson, J. Org. Chem. 1995, 60, 1326.
58. a) C. Copéret, H. Adolfsson, T.-A. V. Khuong, A. K. Yudin, K. B. Sharpless, J. Org. Chem. 1998, 63, 1742;
59. b) C. Copéret, H. Adolfsson, J. P. Chiang, A. K. Yudin. K. B. Sharpless, Tetrahedron Lett. 1998, 39, 761.
60. M. M. Abu-Omar, P. J. Hansen, J. H. Espenson, J. Am. Chem. Soc. 1996, 118, 4966.
61. J. S. M. Wai, I. Markó, J. S. Svendsen, M. G. Finn, E. N. Jacobsen, K. B. Sharpless, J. Am. Chem. Soc. 1989, 111, 1123.
62. An elegant example using the combination of palladium, osmium, tungsten, embedded in a layered double hydroxide matrix, for the tandem Heck- and dihydroxylation reaction was recently reported. In this procedure NMM is required as a co-catalyst. B. M. Choudary, N. S. Chowdari, S. Madhi, M. L. Kantam, Angew. Chem. 2001, 113, 4755; Angew. Chem. Int. Ed. 2001, 40, 4620.
63. An elegant example using the combination of palladium, osmium, tungsten, embedded in a layered double hydroxide matrix, for the tandem Heck- and dihydroxylation reaction was recently reported. In this procedure NMM is required as a co-catalyst. B. M. Choudary, N. S. Chowdari, S. Madhi, M. L. Kantam, Angew. Chem. 2001, 113, 4755; Angew. Chem. Int. Ed. 2001, 40, 4620.
64. We have previously observed that when m-chloroperoxybenzoic acid (mCPBA) was employed as the oxidizing agent, a mixture of the mono-N-oxide and the di-N-oxide was obtained.
65. Y. Ogino, H. Chen, H.-L. Kwong, K. B. Sharpless, Tetrahedron Lett. 1991, 32, 3965.