Asymmetric Electroreduction of Ketone and Aldehyde Derivatives to the Corresponding Alcohols Using Alcohol Dehydrogenase as an Electrocatalyst

Journal of Organic Chemistry

Volumn 62, Issue 8, 1997, Pages 2494-2499

  Yuan, Ruo ^a   Watanabe, Shozo ^a   Kuwabata, Susumu ^a   Yoneyama, Hiroshi ^a  

^a OSAKA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000453593     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9620573     Document Type: Article

References (47)

1. For example: Jones, J. B.; Beck, J. F. In Techniques of Chemistry; Weissberger, A., Ed.; John Wiley and Sons, Inc.: New York, 1975; Vol. X and references cited therein.
2. Jones, J. B. Tetrahedron 1986, 3351.
3. Klibanov, A. M. Science 1983, 219, 722.
4. Battersby, A. R. Chem. Ber. 1984, 611.
5. Parida, S.; Datta, R.; Dordick, J. S. Appl. Biochem. Biotechnol. 1992, 33, 1.
6. Grunwald, J.; Scollar, Beat Wirz, M. P.; Klibanov, A. M. J. Am. Chem. Soc. 1986, 108, 6732.
7. Heidlas, J. E.; Williams, K. W.; Whitesides, G. M. Acc. Chem. Res. 1992, 25, 307.
8. Whitesides, G. M.; Wong, C. H. Angew. Chem. 1985, 97, 617.
9. Kim, M. J.; Whitesides, G. M. J. Am. Chem. Soc. 1988, 110, 2959.
10. Shaked, Z.; Barber, J. J.; Whitesides, G. M. J. Org. Chem. 1981, 46, 4100.
11. DiCosmo, R.; Wong, C. H.; Daniels, L.; Whitesides, G. M. J. Org. Chem. 1981, 46, 4622.
12. Wienkamp, R.; Steckhan, E. Angew. Chem., Int. Ed. Engl. 1982, 21, 782.
13. Maeda, H.; Kajiwara, S. Biotechnol. Bioeng. 1985, 27, 596.
14. Osa, T.; Kashiwagi, Y.; Yanagisawa, Y. Chem. Lett. 1994, 367.
15. Blade, A.-E.; Bourdillon, C.; Laval, J.-M.; Mairesse, G.; Moiroux, J. J. Am. Chem. Soc. 1992, 114, 893.
16. Seegopaul, P.; Rechnitz, G. A. Anal. Chem. 1983, 55, 1929.
17. Cass, A. E. G.; Davis, G.; Francis, G. D.; Hill, H. A. O.; Aston, W. J.; Higgins, I. J.; Plotkin, E. V.; Scott, L. D. L.; Turner, A. P. F. Anal. Chem. 1984, 56, 1889.
18. Foulds, N. C.; Lowe, C. R. J. Chem. Soc., Faraday Trans, 1 1986, 82, 1259.
19. Liaudet, E.; Battaglini, F.; Calvo, E. J. J. Electroanal. Chem. 1990, 293, 55.
20. Bartlett, P. N.; Cooper, J. M. J. Electroanal. Chem. 1993, 362, 1.
21. Degani, Y.; Heller, A. J. Am. Chem. Soc. 1988, 110, 2615.
22. Ohara, T. J.; Rajagopalan, R.; Heller, A. Anal. Chem. 1993, 65, 3512.
23. Iwakura, C.; Kajiya, Y.; Yoneyama, H. J. Chem. Soc., Chem. Commun. 1988, 1019.
24. Kajiya, Y.; Sugai, H.; Iwakura, C.; Yoneyama, H. Anal. Chem. 1991, 63, 49.
25. Kuwabata, S.; Okamoto, T.; Kajiya, Y.; Yoneyama, H. Anal. Chem. 1995, 67, 1684.
26. Jakovak, I. J.; Goodbrand, H. B.; Lok, K. P.; Jones, J. B. J. Am. Chem. Soc. 1982, 104, 4659.
27. Bridges, A. J.; Raman, P. S.; Ng, G. S. Y.; Jones, J. B. J. Am. Chem. Soc. 1984, 106, 1461.
28. Ikeda, T.; Katasho, I.; Senda, M. Anal. Sci. 1988, 4, 133.
29. Kano, K.; Ohgaru, T.; Nakase, H.; Ikeda, T. Chem. Lett. 1996, 439.
30. Sugimura, K.; Kuwabata, S.; Yoneyama, H. J. Am. Chem. Soc. 1989, 111, 2361.
31. Sugimura, K.; Kuwabata, S.; Yoneyama, H. Bioelectrochem. Bioenerg. 1990, 24, 241.
32. Kuwabata, S.; Tsuda, R.; Nishida, K.; Yoneyama, H. Chem. Lett. 1993, 1631.
33. Kuwabata, S.; Tsuda, R.; Yoneyama, H. J. Am. Chem. Soc. 1994, 116, 5437.
34. Kuwabata, S.; Nishida, K.; Yoneyama, H. Chem. Lett. 1994, 407.
35. Yuan, R.; Kuwabata, S.; Yoneyama, H. Chem. Lett, 1996, 137.
36. Nakamura, K.; Aizawa, M.; Miyawaki, O. In Biotechnology Monograph; Aiba, S., Fan, L. T., Fiechter, A., Klein, J., Schugerl, K., Eds.; Springer-Verlag: Berlin, 1988; Vol. 4.
37. Jones, J. B.; Sneddon, D. W.; Higgins, W.; Lewis, A. J. J. Chem. Soc., Chem. Commun. 1972, 856.
38. Taylor, K. E.; Jones, J. B. J. Am. Chem. Soc. 1976, 98, 5689.
39. Pollak, A.; Baughn, R. L.; Whitesides, G. M. J. Am. Chem. Soc. 1977, 99, 2366.
40. Abril, O.; Whitesides, G. M. J. Am. Chem. Soc. 1982, 104, 1552.
41. Wienkamp, R.; Steckhan, E. Angew. Chem., Int. Ed. Engl. 1982, 21, 782.
42. Ito, M.; Kuwana, T. J. Electroanal. Chem. 1971, 32, 415.
43. Matsue, T.; Chang, H. C.; Uchida, I.; Osa, T. Tetrahedron Lett. 1988, 29, 1551.
44. Eliel, E.; Otsuka, S. Asymmetric Reactions and Processes; American Chemical Society: Washington, DC, 1982; p 187.
45. Evans, D. H. In Encyclopedia of Electrochemistry of the Elements; Bard, A. J., Ed.; Marcel Dekker: New York, 1978; Vol. XII, Chapter XII-1, p 1.
46. Prelog, V. Pure Appl. Chem. 1964, 9, 119.
47. Lamed, R. J.; Keinan, E.; Zeikus, J. G. Enzyme Microb. Technol. 1981, 3, 144.