Chemo- and enantioselective routes to chiral fluorinated hydroxyketones using ketoreductases

Organic Letters

Volumn 9, Issue 24, 2007, Pages 4951-4954

  Grau, Brendan T ^a   Devine, Paul N ^a   DiMichele, Lisa N ^a   Kosjek, Birgit ^a  

^a MERCK RESEARCH LABORATORIES   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

FLUORINATED HYDROCARBON; KETONE; OXIDOREDUCTASE;

ARTICLE; CATALYSIS; CHEMISTRY; STEREOISOMERISM; SYNTHESIS; TIME;

CATALYSIS; HYDROCARBONS, FLUORINATED; KETONES; OXIDOREDUCTASES; STEREOISOMERISM; TIME FACTORS;

EID: 36849056594     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol701810v     Document Type: Article

References (23)

1. Thayer, A. M. Chem. Eng. News 2006, 84, 15-24.
2. Swinson, J. PharmaChem 2007, 6, 4, 38-41;
3. Swinson, J. Pharma-Chem 2005, 4, 6, 26-30.
4. Sasaki, S.; Yamauchi, T.; Kubo, H.; Kanai, M.; Ishii, A.; Higashiyama, K. Tetrahedron Lett. 2005, 46, 1497-1500.
5. Hess, R.; Diezi, S.; Mallat, T.; Baiker. A. Tetrahedron: Asymmetry 2004, 15, 251-257.
6. Boutante, P.; Mousset, G.; Veschambre, H. New J. Chem. 1998, 247-251.
7. Mahmoodi, N. O.; Mohammadi, H. G. Monatsh. Chem. 2003, 134, 1283-1288.
8. Edegger, K.; Stampfer, W.; Seisser, B; Faber, K; Mayer, S. F.; Oehrlein, R.; Hafner, A.; Kroutil, W. Eur. J. Org. Chem. 2006, 1904-1909.
9. Muller, M.; Wolberg, M.; Shubert, T.; Hummel, W. Adv. Biochem. Eng. Biotechnol. 2005, 92, 261-287.
10. Wolberg, M.; Hummel, W.; Wandrey, C.; Muller, M. Angew. Chem., Int. Ed. 2000, 39, 23, 4306-4308.
11. Zhu, D.; Rios, B. D.; Rozzell, J. D.; Hua, L. Tetrahedron: Asymmetry 2005, 16, 1541-1546.
12. Groger, H.; Hummel, W.; Rollman, C.; Chamouleau, F.; Husken, H.; Werner, H.; Wunderlich, C.; Abokitse, K.; Drauz, K.; Buchholz, S. Tetrahedron 2004, 60, 633-640.
13. Rosen, T. C.; Feldmann, R.; Dunkelmann, P.; Daubmann, T. Tetrahedron Lett. 2006, 47, 4803-4806.
14. Pollard, D.; Truppo, M.; Pollard, J.; Chen, C.; Moore, J. Tetrahedron: Asymmetry 2006, 17, 554-559.
15. Yamazaki, Y.; Kobayashi, H. Tetrahedron: Asymmetry 1993, 6, 1287-1294.
16. Bradshaw, C. W.; Hummel, W.; Wong, C. H. J. Org. Chem. 1992, 57, 1532-1536.
17. Caron, D.; Coughlan, A. P.; Simard, M.; Bernier, J.; Piche, Y.; Chenevert, R. Biotechnol. Lett. 2005, 27, 713-716.
18. +, NADH, and NADPH were purchased from Biocatalytics, Inc. (Pasedena, Ca, U.S.A.). ADH CDX0101, ADH CDX013, alcohol dehydrogenase from Lactobacillus brevis (ADH-LB), and alcohol dehydrogenase from Thermoanaerobacter sp. (ADH T) were purchased from Julich Chiral Solutions, Ine (Julich, Germany). All chemicals used were certified as reagent grade and purchased from Sigma-Aldrich and Fisher Scientific. Screening conditions are listed in Tables 1 and 2 under footnote "a".
19. Wu, J. T.; Wu, L. H.; Knight, J. A. Clin. Chem. 1986, 3, 314-319.
20. Hummel, W.; Riebel, B. Biotechnol. Lett. 2003, 25, 51-54.
21. Timperley, C M.; White, W. E. J. Fluorine Chem. 2003, 123, 65-70.
22. Xiao, L.; Yamazaki, T.; Kitazume, T.; Yonezawa, T.; Sakamoto, Y.; Nogawa, K. J. Fluorine Chem. 1997, 84, 19-23.
23. Homann, M. J.; Vail, R. B.; Previte, E.; Tamarez, M.; Morgan, B.; Dodds, D. R.; Zaks, A. Tetrahedron. 2004, 60, 789-797.