A new coupled catalytic system for dihydroxylation of olefins by H2O2 [5]

Journal of the American Chemical Society

Volumn 121, Issue 44, 1999, Pages 10424-10425

  Bergstad, Katarina ^a   Jonsson, Sandra Y ^b   Bäckvall, Jan E ^b  

^a UPPSALA UNIVERSITY   (Sweden)

^b STOCKHOLM UNIVERSITY   (Sweden)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE DERIVATIVE; HYDROGEN PEROXIDE;

CATALYSIS; CATALYST; ELECTRON TRANSPORT; HYDROXYLATION; LETTER; OXIDATION;

EID: 0033544364     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja991710b     Document Type: Letter

References (37)

1. (a) Simándi, L. I. Catalytic Activation of Dioxygen by Metal Complexes; Kluwer: Dordrecht, The Netherlands, 1992.
2. (b) Strukul, G. Catalytic Oxidations with Hydrogen Peroxide as Oxidant; Kluwer: Dordrecht, The Netherlands, 1992.
3. (a) Moser, C. C.; Keske, J, M.; Warncke, K.; Faird, R. S.; Dutton, P. L. Nature 1992, 355, 796-802.
4. (b) Nugent, J. H. A. Eur. J. Biochem. 1996, 237, 519-31.
5. (c) Hughes, M. N. The Inorganic Chemistry of Biological Processes; Wiley: Chichester, UK, 1981.
6. (a) Smidt, J.; Hafner, W.; Jira, R.; Sedlmeier, J.; Sieber, R.; Rüttinger, R.; Kojer, H. Angew. Chem. 1959, 71, 176.
7. (b) Tsuji, J. Palladium Reagents and Catalysts. Innovations in Organic Synthesis; Wiley: Chichester, UK, 1995.
8. (c) Bäckvall, J. E.; Åkermark, B.; Ljunggren, S. O. J. Am. Chem. Soc. 1979, 101, 2411-2416.
9. (a) Bäckvall, J. E.; Hopkins, R. B.; Grennberg, H.; Mader, M. M.; Awasthi, A. K. J. Am. Chem. Soc. 1990, 112, 5160-5166.
10. (b) Grennberg, H.; Faizon, S.; Bäckvall, J. E. Angew. Chem., Int. Ed. Engl. 1993, 32, 263-264.
11. (a) Bäckvall, J. E.; Chowdhury, R. L.; Karlsson, U. J. Chem. Soc., Chem. Commun. 1991, 473-475.
12. (b) Wang, G.-Z.; Andreasson, U.; Bäckvall, J. E. J. Chem. Soc., Chem. Commun. 1994, 1037-1038.
13. For aerobic electron transfer-based oxidations developed by others see: (a) Byström, S. E.; Larsson, E. M.; Åkermark, B. J. Org. Chem. 1990, 55, 5674. (b) Yokota, T.; Sakurai, Y.; Sakaguchi, S.; Ishii, Y. Tetrahedron Lett. 1997, 38, 3923-3926.
14. For aerobic electron transfer-based oxidations developed by others see: (a) Byström, S. E.; Larsson, E. M.; Åkermark, B. J. Org. Chem. 1990, 55, 5674. (b) Yokota, T.; Sakurai, Y.; Sakaguchi, S.; Ishii, Y. Tetrahedron Lett. 1997, 38, 3923-3926.
15. Schröder, M. Chem. Rev. 1980, 80, 187-213.
16. (a) Sharpless, K. B.; Akashi, K. J. Am. Chem. Soc. 1976, 98, 1986-1987.
17. (b) Akashi, K.; Palermo, R. E.; Sharpless, K. B. J. Org. Chem. 1978, 43, 2063-2066.
18. (a) VanRheenen, V.; Kelly, R. C.; Cha, D. Y. Tetrahedron Lett. 1976, 1973-1976.
19. (b) VanRheenen, V.; Cha, D. Y.; Hartley, W. M. Org. Synth. 1988, Collect. Vol. VI, 342-348.
20. Kolb, H. C.; VanNieuwenhze, M. S.; Sharpless, K. B. Chem. Rev. 1994, 94, 2483-2547.
21. (a) Wai, J. S. M.; Markó, I.; Svendsen, J. S.; Finn, M. G.; Jacobsen, E. N.; Sharpless, K. B. J. Am. Chem. Soc. 1989, 111, 1123.
22. (b) Sharpless, K. B.; Amberg, W.; Bennani, Y. L.; Crispino, 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.
23. (c) Ahrgren, L.; Sutin, L. Org. Proc. Res. Develop. 1997, 1, 425-427.
24. 2 as the terminal oxidant: (a) Milas, N. A.; Sussman, S. J. Am. Chem. Soc. 1936, 58, 1302-1305. (b) Milas, N. A.; Sussman, S. J. Am. Chem. Soc. 1937, 59, 2345-2347. (c) Milas, N. A.; Sussman, S.; Mason, H. S. J. Am. Chem. Soc. 1939, 61, 1844-1847. (d) Milas, N. A.; Trepagnier, J. H.; Nolan, J. T.; Iliopulos, M. I. J. Am. Chem. Soc. 1959, 81, 4730-4733.
25. 2 as the terminal oxidant: (a) Milas, N. A.; Sussman, S. J. Am. Chem. Soc. 1936, 58, 1302-1305. (b) Milas, N. A.; Sussman, S. J. Am. Chem. Soc. 1937, 59, 2345-2347. (c) Milas, N. A.; Sussman, S.; Mason, H. S. J. Am. Chem. Soc. 1939, 61, 1844-1847. (d) Milas, N. A.; Trepagnier, J. H.; Nolan, J. T.; Iliopulos, M. I. J. Am. Chem. Soc. 1959, 81, 4730-4733.
26. 2 as the terminal oxidant: (a) Milas, N. A.; Sussman, S. J. Am. Chem. Soc. 1936, 58, 1302-1305. (b) Milas, N. A.; Sussman, S. J. Am. Chem. Soc. 1937, 59, 2345-2347. (c) Milas, N. A.; Sussman, S.; Mason, H. S. J. Am. Chem. Soc. 1939, 61, 1844-1847. (d) Milas, N. A.; Trepagnier, J. H.; Nolan, J. T.; Iliopulos, M. I. J. Am. Chem. Soc. 1959, 81, 4730-4733.
27. 2 as the terminal oxidant: (a) Milas, N. A.; Sussman, S. J. Am. Chem. Soc. 1936, 58, 1302-1305. (b) Milas, N. A.; Sussman, S. J. Am. Chem. Soc. 1937, 59, 2345-2347. (c) Milas, N. A.; Sussman, S.; Mason, H. S. J. Am. Chem. Soc. 1939, 61, 1844-1847. (d) Milas, N. A.; Trepagnier, J. H.; Nolan, J. T.; Iliopulos, M. I. J. Am. Chem. Soc. 1959, 81, 4730-4733.
28. 2: Bergstad, K.; Bäckvall, J. E. J. Org. Chem. 1998, 63, 6650-6655.
29. Bergstad, K.; Piet, J. J. N.; Bäckvall, J. E. J. Org. Chem. 1999, 64, 2545-2548.
30. 4a
31. 2 with related flavins to give flavin hydroperoxides see: (a) Kemal, C.; Bruice, T. C. Proc. Natl. Acad. Sci. U.S.A. 1976, 73, 995. (b) Mager, H. I. X.; Berends, W. Tetrahedron 1976, 32, 2303.
32. 2 with related flavins to give flavin hydroperoxides see: (a) Kemal, C.; Bruice, T. C. Proc. Natl. Acad. Sci. U.S.A. 1976, 73, 995. (b) Mager, H. I. X.; Berends, W. Tetrahedron 1976, 32, 2303.
33. 2 oxidations were carried out according to the procedure by Milas (see ref 12).
34. 2 (2.5 h) in the oxidation of 1 did not result in any considerable change in the reaction outcome, and the diol 2 was isolated in 83% yield.
35. 11b,19b has been tested so far.
36. 2PHAL = hydroquinidine 1,4-phthalazinediyl diether.
37. In this case it was necessary to change solvent to t-BuOH since the oxidation in acetone gave a lower ee. Also, the olefin had to be added slowly (over 9 h), since addition of all olefin at once gave only 74% ee. Optimization of the enantioselectivity for different olefins with the present system will require further studies (variation of solvent, addition time, temperature, etc).