Ruthenium-Catalyzed Cytochrome P-450 Type Oxidation of Tertiary Amines with Alkyl Hydroperoxides

Journal of the American Chemical Society

Volumn 110, Issue 24, 1988, Pages 8256-8258

  Murahashi, Shun Ichi ^a   Naota, Takeshi ^a   Yonemura, Koichi ^a  

^a OSAKA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000638447     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja00232a060     Document Type: Article

References (15)

1. Cytochrome P-450; Sato, R., Omura, T., Eds.; Kodansha Ltd: Tokyo, 1978. (b) Gorrod, J. W. Biological Oxidation of Nitrogen; Elsevier/North Holland Biomedical Press: New York, 1978.
2. Shannon, P.; Bruice, T. C. J. Am. Chem. Soc. 1981, 103, 4580. (b) Dicken, C. M.; Lu, F.-L.; Nee, M. W.; Bruice, T. C. J. Am. Chem. Soc. 1985, 107, 5776. (c) Ostovic, D.; Knobler, C. B.; Bruice, T. C. J. Am. Chem. Soc. 1987, 109, 3444.
3. Santa, T.; Miyata, N.; Hirobe, M. Chem. Pharm. Bull. 1984, 32, 1252. (b) Fujimori, K.; Fujiwara, S.; Takata, T.; Oae, S. Tetrahedron Lett. 1986, 27, 581. (c) Lindsay Smith, J. R.; Mortimer, D. N. J. Chem. Soc., Chem. Commun. 1985, 64.
4. Murahashi, S.-I.; Hirano, T.; Yano, T. J. Am. Chem. Soc. 1978, 100, 348. (b) Murahashi, S.-I.; Watanabe, T. J. Am. Chem. Soc. 1979, 101, 7429. (c) Murahashi, S.-I.; Yoshimura, N.; Tsumiyama, T.; Kojima, T. J. Am. Chem. Soc. 1983, 105, 5002. (d) Mitsui, H.; Zenki, S.; Shiota, T.; Murahashi, S.-I. J. Chem. Soc., Chem. Commun. 1984, 874. (e) Murahashi, S.-I.; Naota, T.; Taki, H. J. Chem. Soc., Chem. Commun. 1985, 613.
5. Sheldon, R. A.; Kochi, J. K. Metal-Catalyzed Oxidations of Organic Compounds; Academic Press: New York, 1981; p 387.
6. Shono, T.; Toda, T.; Oshino, N. J. Am. Chem. Soc. 1982, 104, 2639. (b) Miwa, G. T.; Garland, W. A.; Hodshon, B. J.; Lu, A. Y. H.; Northrop, D. B. J. Biol. Chem. 1980, 255, 6049. (c) Miwa, G. T.; Walsh, J. S.; Kedderis, G. L.; Hollenberg, P. F. J. Am. Chem. Soc. 1983, 258, 14445.
7. Thompson, J. A.; Holtzman, J. L. Drug Metab. Dispos. 1974, 2, 577. (b) Reference 8b.
8. Heimbrook, D. C.; Murray, R. I.; Egeberg, K. D.; Sligar, S. G.; Nee, M. W.; Bruice, T. C. J. Am. Chem. Soc. 1984, 106, 1514. (b) Burka, L. T,; Guengerich, F. P.; Willard, R. J.; Macdonald, T. L. J. Am. Chem. Soc. 1985, 107, 2549.
9. Marmion, L. E.; Takeuchi, K. J. J. Am. Chem. Soc. 1986, 108, 510. (b) Roecker, L.; Meyer, T. J. J. Am. Chem. Soc. 1987, 109, 746.
10. Groves, J. T.; Watanabe, Y. J. Am. Chem. Soc. 1986, 108, 7834.
11. N-Dealkylation with a stoichiometric amount of oxidants is nonselective: Rosenblatt, D. H.; Burrows, E. P. In The Chemistry of Amino, Nitroso and Nitro Compounds and Their Derivatives, Part 2; Patai, S., Ed., Wiley: New York, 1982; Chapter 25.
12. Cordell, G. A. Introduction to Alkaloids: A Biogenetic Approach; Wiley: New York, 1981; Chapter 8.
13. Larsen, S. D.; Grieco, P. A.; Fobare, W. F. J. Am. Chem. Soc. 1986, 108, 3512, and references cited therein, (b) Doedens, R. J.; Meier, G. P.; Overman, L. E. J. Org. Chem. 1988, 53, 685.
14. Hiemstra, H.; Fortgens, H. P.; Speckamp, W. N. Tetrahedron Lett. 3155. 1985
15. Flann, C. J.; Overman, L. E. J. Am. Chem. Soc. 1987, 109, 6115. (b) Speckamp, W. N. Recl. Trav. Chim. Pays-Bas 1981, 100, 345, and references cited therein.