Microbial and homogenous asymmetric catalysis in the reduction of 1-[3,5-bis(trifluoromethyl)phenyl]ethanone

Tetrahedron Asymmetry

Volumn 17, Issue 13, 2006, Pages 2000-2005

  Gelo Pujic, Mirjana ^a   Le Guyader, Frédéric ^a   Schlama, Thierry ^a  

^a Rhodia Europe   (France)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOL; HYDROGEN; LIGAND;

ARTICLE; ASYMMETRIC CATALYSIS; ENANTIOMER; ENZYME ACTIVATION; MICROORGANISM DETECTION; NONHUMAN; PRIORITY JOURNAL; PROTON TRANSPORT; REDUCTION;

EID: 33747019503     PISSN: 09574166     EISSN: 1362511X     Source Type: Journal    
DOI: 10.1016/j.tetasy.2006.06.033     Document Type: Article

References (46)

1. Hirama M., Shimizu H., and Iwashita M. J. Chem. Soc., Chem. Commun. 10 (1983) 599-600
2. Brooks D.W., Kellogg R.P., and Cooper C.S. J. Org. Chem. 52 (1987) 192-196
3. Fuganti C., Grasselli P., Casati P., and Carmeno M. Tetrahedron Lett. 26 (1985) 101-104
4. Rodriguez S., Kayser M.M., and Stewart J.D. J. Am. Chem. Soc. 123 (2001) 1547-1556
5. Fauve A., and Veschambre H. Tetrahedron Lett. 28 (1987) 5037-5040
6. Chenevert R., and Thiboutot S. Can. J. Chem. 64 (1986) 1599-1601
7. Ohta H., Ozaki K., and Tsuchihashi G. Chem. Lett. (1987) 191-192
8. Bortolini O., Fantin G., Fogagnolo M., Giovannini P.P., Guerrini A., and Medici A. J. Org. Chem. 62 (1997) 1854-1856
9. Bernardi R., Cardillo R., and Ghiringhelli D. J. Chem. Soc., Chem. Commun. 7 (1984) 460-461
10. Jönsson A., Wehtje E., Adlercreutz P., and Mattiasson B. Biochim. Biophys. Acta 1430 (1999) 313-322
11. Belan A., Bolte J., Fauve A., Gourey J.G., and Veschambre H. J. Org. Chem. 52 (1987) 256-260
12. Shimizu S., Kataoka M., and Kita K. J. Mol. Catal. B: Enzym. 5 (1998) 321-325
13. Crumbie R.L., Deol B.S., Nemorin J.E., and Ridley D.D. Aust. J. Chem. 31 (1978) 1965-1980
14. Crumbie R.L., Ridley D.D., and Simpson G.W. J. Chem. Soc., Chem. Commun. 9 (1977) 315-316
15. Newton R.F., and Roberts S.M. Tetrahedron 36 (1980) 2163-2196
16. Lowe G., and Swain S.. J. Chem. Soc., Perkin Trans. 1 (1985) 391-398
17. Gramatica P., Manitto P., and Poli L. J. Org. Chem. 50 (1985) 4625-4628
18. D'Arrigo P., Lattanzio M., Fantoni G.P., and Servi S. Tetrahedron: Asymmetry 9 (1998) 4021-4026
19. Shieh W.R., Gopalan A.S., and Sih C.J. J. Am. Chem. Soc. 107 (1985) 2993-2994
20. Seebach D., Roggo S., Maetzke T., Braunschwieger H., Cercus J., and Krieger M. Helv. Chim. Acta 70 (1987) 1605-1615
21. Servi S. Synthesis (1990) 1-25
22. Prelog V. Pure Appl. Chem. 9 (1964) 119-130
23. Nakamura K., Inoue Y., and Ohno A. Tetrahedron Lett. 36 (1995) 265-266
24. Matsuda T., Harada T., Nakajima N., Itoh T., and Nakamura K. J. Org. Chem. 65 (2000) 157-163
25. Hummel W. Appl. Microbiol. Biotechnol. 34 (1990) 15-19
26. Hummel W. TIBTECH 17 (1999) 487-492
27. Patel R.N., Banerjee A., Liu M., Hanson R., Ko R., Howell J., and Szarka L.J. Biotechnol. Appl. Biochem. 17 (1993) 139-153
28. Nakamura K., and Matsuda T. J. Org. Chem. 63 (1998) 8957-8964
29. Bradshaw C.W., Hummel W., and Wong C.-H. J. Org. Chem. 57 (1992) 1532-1536
30. Bradshaw C.W., Fu H., Shen G.-J., and Wong C.-H. J. Org. Chem. 57 (1992) 1526-1532
31. Takano S., Yanase M., Sekiguchi Y., and Ogasawara K. Tetrahedron Lett. 28 (1987) 1783-1784
32. Manzoochi A., Casati R., Fiecchi A., and Santaniello E. J. Chem. Soc., Perkin Trans. 1 (1987) 2753-2757
33. Lis R., Caldwell W.B., Hoyer G.A., and Petzoldt K. Tetrahedron Lett. 28 (1987) 1487-1490
34. Hashiguchi S., Fujii A., Tekehara J., Ikariya T., and Noyori R. J. Am. Chem. Soc. 117 (1995) 7562-7563
35. Hashiguchi S., Fujii A., Uematsu N., Ikariya T., and Noyori R. J. Am. Chem. Soc. 118 (1996) 2521-2522
36. Hashiguchi S., and Noyori R. Acc. Chem. Res. 30 (1997) 97-102
37. Haack K.-J., Hashiguchi S., Fujii A., Ikariya T., and Noyori R. Angew. Chem., Int. Ed. 36 (1997) 285-288
38. Yamakawa M., Ito H., and Noyori R. J. Am. Chem. Soc. 122 (2000) 1466-1478
39. Yamakawa M., Yamada I., and Noyori R. Angew. Chem., Int. Ed. 40 (2001) 2818-2821
40. Kramer M.S., Cutler N., Feighner J., Shrivastava R., Carman J., Sramek J.J., Reines S.A., Liu G., Snavely D., Wyatt K.E., Hale J.J., Mills S.G., MacCoss M., Swain C.J., Harrison T., Hill R.G., Hefti F., Scolnik E.M., Cascieri M.A., Chicchi G.G., Sadowski S., Williams A.R., Hewson L., Smith D., and Rupniak N.M. Science 281 (1998) 1640-1645
41. Nakamura K., Takano S., Terada K., and Ohno A. Chem. Lett. 21 (1992) 951-954
42. Griffin D.R., Yang F., Carta G., and Gainer J.L. Biotechnol. Prog. 14 (1998) 588-593
43. Devine, P.; Hansen, K. WO 01/02326, for Merck & Co. (priority data 01/07/1999).
44. Le Guyader, F. Internal report 'Réduction Asymétrique de Cétones Aromatiques par Transfert d'Hydrure', 2002.
45. Wills M., Gamble M., Palmer M., Smith A., Studley J., and Kemy J. J. Mol. Catal. A: Chem: 146 (1999) 139-148
46. Halle R., Breheret A., Schulz E., Pinel C., and Lemaire M. Tetrahedron: Asymmetry 8 (1997) 2101-2108