Continuous-flow asymmetric biomimetic transamination

Journal of Fluorine Chemistry

Volumn 130, Issue 5, 2009, Pages 512-515

  Soloshonok, Vadim A ^a,b   Catt, Hector T ^a,b   Ono, Taizo ^a,b  

^a NATIONAL INSTITUTE OF ADVANCED INDUSTRIAL SCIENCE AND TECHNOLOGY AIST   (Japan)

^b UNIVERSITY OF OKLAHOMA   (United States)

Author keywords

1,3 Proton shift reaction; Asymmetric synthesis; Biomimetic transamination; Continuous process; Fluorine containing amino compounds; On column reactions; Reductive amination

Indexed keywords

EID: 67349254163     PISSN: 00221139     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jfluchem.2009.02.010     Document Type: Article

References (39)

1. Murahashi S.-I., and Zhang D. Chem. Soc. Rev. 37 (2008) 1490
2. Soloshonok V.A., and Berbasov D.O. J. Fluor. Chem. 125 (2004) 1757
3. Braunshtein A.E., and Kritsman M.G. Biokhimiya (Moscow) 2 (1937) 859
4. Tanner M.E. Acc. Chem. Res. 35 (2002) 237
5. Nagy P., Ueki H., Berbasov D.O., and Soloshonok V.A. J. Fluor. Chem. 129 (2008) 409
6. Liu L., Zhou W., Chruma J., and Breslow R. J. Am. Chem. Soc. 126 (2004) 8136
7. Corey E.J., and Achiwa K. J. Am. Chem. Soc. 91 (1969) 1429
8. Calo V., Lopez L., and Todesco P.E. J. Perkin Trans. 1 (1972) 1652
9. Ohta S., and Okamoto M. Synthesis (1982) 756
10. Babler J.H., and Invergo B.J. J. Org. Chem. 46 (1981) 1937
11. Buckley T.F., and Rapoport H. J. Am. Chem. Soc. 104 (1982) 4446
12. Cainelli G., Giacomini D., Trere A., and Boyl P.P. J. Org. Chem. 61 (1996) 5134
13. Ando M., and Kuzuhara H. Bull. Chem. Soc. Jpn. 63 (1990) 1925
14. Hjelmencrantz A., and Berg U. J. Org. Chem. 67 (2002) 3585
15. Zimmerman S., and Breslow R. J. Am. Chem. Soc. 106 (1984) 1490
16. Soloshonok V.A., Kirilenko A.G., Kukhar V.P., and Resnati G. Tetrahedron Lett. 35 (1994) 3119
17. Soloshonok V.A., and Ono T. Synletter (1996) 919
18. Soloshonok V.A., and Ono T. Tetrahedron 52 (1996) 14701
19. Ohkura H., Berbasov D.O., and Soloshonok V.A. Tetrahedron Lett. 44 (2003) 2417
20. Ohkura H., Berbasov D.O., and Soloshonok V.A. Tetrahedron 59 (2003) 1647
21. Berbasov D.O., Ojemaye I.D., and Soloshonok V.A. J. Fluor. Chem. 125 (2004) 603
22. Soloshonok V.A., Ohkura H., and Yasumoto M. J. Fluor. Chem. 127 (2006) 708
23. Soloshonok V.A., and Yasumoto M. J. Fluor. Chem. 127 (2006) 889
24. Yasumoto M., Ueki H., and Soloshonok V.A. J. Fluor. Chem. 128 (2007) 736
25. Soloshonok V.A., and Kukhar V.P. Tetrahedron 53 (1997) 8307
26. Yuan C., Li S., and Xiao J. Heteroatom Chem. 11 (2000) 541
27. Soloshonok V.A., Kirilenko A.G., Kukhar V.P., and Resnati G. Tetrahedron Lett. 34 (1993) 3621
28. Soloshonok V.A., Kirilenko A.G., Fokina N.A., Galushko S.V., Kukhar V.P., Svedas V.K., and Resnati G. Tetrahedron: Asymmetry 5 (1994) 1225
29. Soloshonok V.A., Avilov D.V., and Kukhar V.P. Tetrahedron: Asymmetry 7 (1996) 1547
30. Soloshonok V.A., and Kukhar V.P. Tetrahedron 52 (1996) 6953
31. Xiao J., Zhang X., and Yuan C. Heteroatom Chem. 11 (2000) 536
32. Soloshonok V.A., Ohkura H., and Uneyama K. Tetrahedron Lett. 43 (2002) 5449
33. Michaut V., Metz F., Paris J.M., and Plaquevent J.C. J. Fluor. Chem. 128 (2007) 500
34. Soloshonok V.A., Kirilenko A.G., Galushko S.V., and Kukhar V.P. Tetrahedron Lett. 35 (1994) 5063
35. Soloshonok V.A., Ohkura H., and Yasumoto M. J. Fluor. Chem. 127 (2006) 924
36. Soloshonok V.A., Ohkura H., and Yasumoto M. J. Fluor. Chem. 127 (2006) 930
37. Soloshonok V.A., and Yasumoto M. J. Fluor. Chem. 128 (2007) 170
38. Soloshonok V.A., and Ono T. J. Fluor. Chem. 129 (2008) 785
39. Typical set up of the column and experiment: a glass column (3.9 cm × 104 cm) was charged with 260 g of silica gel (hexanes). While leaving about 1 cm of the solvent on top of silica gel, a suspension of 130 g of silica gel in dichloromethane containing 1.3 g of DBU was charged onto the top and allowed to percolate down to the surface of silica gel. Finally, additional 150 g of silica gel (hexanes) was added on the top of the column allowing the solvent to percolate down to the surface of silica gel completely. A heating mantle was attached to the column covering fully the corresponding "reaction zone" and about half of the "protection zone"; the temperature was set at 50 °C. Using thus prepared column, a solution [10 mol% in hexanes/acetonitrile (4/1)] of fluorinated imines 16a-e was eluted through the column at the rate of 1 drop per second. UV-active fractions (detection by TLC) were collected and evaporated to afford products 16a-e (for yields and enantioselectivity, see Scheme 4).