First example of continuous-flow reaction conditions for biomimetic reductive amination of fluorine-containing carbonyl compounds

Journal of Fluorine Chemistry

Volumn 129, Issue 9, 2008, Pages 785-787

  Soloshonok, Vadim A ^a,b   Ono, Taizo ^a  

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

^b UNIVERSITY OF OKLAHOMA   (United States)

Author keywords

1,3 Proton shift reaction; Continuous flow reactions biomimetic reductive amination; Fluorinated amino compounds; On column reactions

Indexed keywords

EID: 50549091408     PISSN: 00221139     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jfluchem.2008.05.019     Document Type: Article

References (76)

1. Braunshtein A.E., and Kritsman M.G. Biokhimiya (Moscow) 2 (1937) 859-874
2. Martell A.E. Acc. Chem. Res. 22 (1989) 115-124
3. Tanner M.E. Acc. Chem. Res. 35 (2002) 237-246
4. Wachtershauser G. Microbiol. Rev. 52 (1988) 452-484
5. Liu L., Zhou W., Chruma J., and Breslow R. J. Am. Chem. Soc. 126 (2004) 8136-8137
6. Liu L., and Breslow R. J. Am. Chem. Soc. 125 (2003) 12110-12111
7. Zabinski R.F., and Toney M.D. J. Am. Chem. Soc. 123 (2001) 193-198
8. Ogo S., Uehara K., Abura T., and Fukuzumi S. J. Am. Chem. Soc. 126 (2004) 3020-3021
9. Longenecker J.B., and Snell E.E. J. Am. Chem. Soc. 79 (1957) 142-145
10. Casella L., and Gullotti M. J. Am. Chem. Soc. 105 (1983) 803-809
11. Liu L., Rozenman M., and Breslow R. J. Am. Chem. Soc. 124 (2002) 12660-12661
12. Liu L., and Breslow R. J. Am. Chem. Soc. 124 (2002) 4978-4979
13. Breslow R., Canary J.W., Varney M., Waddell S.T., and Yang D. J. Am. Chem. Soc. 112 (1990) 5212-5219
14. Jaeger D.A., Broadhurst M.D., and Cram D.J. J. Am. Chem. Soc. 101 (1979) 717-732
15. For review see:. Layer R.W. Chem. Rev. 63 (1963) 489-510
16. Smith P.A.S., and Van Dang C. J. Org. Chem. 41 (1976) 2013-2015
17. Brandenberger H., and Cohen P.P. Helv. Chim. Acta 36 (1953) 549-554
18. Biomimetic oxidative deamination of amines:
19. Corey E.J., and Achiwa K. J. Am. Chem. Soc. 91 (1969) 1429-1432
20. Calo V., Lopez L., and Todesco P.E. J. Perkin Trans. 1 (1972) 1652-1653
21. Ohta S., and Okamoto M. Synthesis (1982) 756-758
22. Babler J.H., and Invergo B.J. J. Org. Chem. 46 (1981) 1937-1938
23. Buckley T.F., and Rapoport H. J. Am. Chem. Soc. 104 (1982) 4446-4450
24. Baddar F.G., and Iskander Z. Nature 167 (1951) 1069-1070
25. Baddar F.G. J. Chem. Soc. (1950) 136-139
26. Baddar F.G., and Iskander Z. J. Chem. Soc. (1954) 203-209
27. Baddar F.G., and Iskander Z. J. Chem. Soc. (1954) 209-213
28. Biomimetic reductive amination of carbonyl compounds:
29. Cainelli G., Giacomini D., Trere A., and Boyl P.P. J. Org. Chem. 61 (1996) 5134-5139
30. Ando M., and Kuzuhara H. Bull. Chem. Soc. Jpn. 63 (1990) 1925-1928 references therein on previous publications
31. Willems J.G.H., de Vries J.G., Nolte R.J.M., and Zwanenburg B. Tetrahedron Lett. 36 (1995) 3917-3920
32. Hjelmencrantz A., and Berg U. J. Org. Chem. 67 (2002) 3585-3594
33. Bachmann S., Knudsen K.R., and Jørgensen K.A. Org. Biomol. Chem. 2 (2004) 2044-2049
34. Zimmerman S., and Breslow R. J. Am. Chem. Soc. 106 (1984) 1490-1491
35. Wu Y., and Ahlberg P. J. Org. Chem. 57 (1992) 6324-6327
36. Wu Y., and Ahlberg P. Acta Chem. Scand. 46 (1992) 60-72
37. Bernauer K., Deschenaux R., and Taura T. Helv. Chim. Acta 66 (1983) 2049-2058
38. Deschenaux R., and Bernauer K. Helv. Chim. Acta 67 (1984) 373-377
39. Biomimetic transamination of fluorinated aldehydes and ketones:
40. Soloshonok V.A., Gerus I.L., Yagupolskii Y.I., and Kukhar V.P. Zh. Org. Khim. 23 (1987) 2308-2313 Chem. Abstr. 109, 55185
41. Soloshonok V.A., Gerus I.L., Yagupolskii Y.I., and Kukhar V.P. Zh. Org. Khim. 24 (1988) 993-997 Chem. Abstr. 110, 134824v
42. Soloshonok V.A., Yagupolskii Y.I., and Kukhar V.P. Zh. Org. Khim. 24 (1988) 1638-1644 Chem. Abstr. 110, 154827b
43. Khotkevich A.B., Soloshonok V.A., and Yagupolskii Y.I. Zh. Obshch. Khim. 60 (1990) 1005-1008 Chem. Abstr. 113, 171274y
44. Soloshonok V.A., Kirilenko A.G., Kukhar V.P., and Resnati G. Tetrahedron Lett. 35 (1994) 3119-3122
45. Soloshonok V.A., and Ono T. Synlett (1996) 919-921
46. Soloshonok V.A., and Ono T. Tetrahedron 52 (1996) 14701-14712
47. Ohkura H., Berbasov D.O., and Soloshonok V.A. Tetrahedron Lett. 44 (2003) 2417-2420
48. Ohkura H., Berbasov D.O., and Soloshonok V.A. Tetrahedron 59 (2003) 1647-1656
49. Berbasov D.O., Ojemaye I.D., and Soloshonok V.A. J. Fluor. Chem. 125 (2004) 603-607
50. Ono T., Kukhar V.P., and Soloshonok V.A. J. Org. Chem. 61 (1996) 6563-6569
51. Soloshonok V.A., Ohkura H., and Yasumoto M. Mendeleev Commun. (2006) 165-167
52. Soloshonok V.A., Ohkura H., and Yasumoto M. J. Fluor. Chem. 127 (2006) 708-711
53. Soloshonok V.A., and Yasumoto M. J. Fluor. Chem. 127 (2006) 889-893
54. Soloshonok V.A., and Berbasov D.O. J. Fluor. Chem. 125 (2004) 1757-1763
55. Yasumoto M., Ueki H., and Soloshonok V.A. J. Fluor. Chem. 128 (2007) 736-739
56. Biomimetic transamination of fluorinated α-keto acids:
57. Soloshonok V.A., and Kukhar' V.P. Tetrahedron 53 (1997) 8307-8314
58. Biomimetic transamination of fluorinated β-keto acids:
59. Soloshonok V.A., Kirilenko A.G., Kukhar V.P., and Resnati G. Tetrahedron Lett. 34 (1993) 3621-3624
60. Soloshonok V.A., Kirilenko A.G., Fokina N.A., Shishkina I.P., Galushko S.V., Kukhar V.P., Svedas V.K., and Kozlova E.V. Tetrahedron: Asymmetry 5 (1994) 1119-1126
61. 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) 1225-1228
62. Soloshonok V.A., and Kukhar V.P. Tetrahedron 52 (1996) 6953-6964
63. "Double" biomimetic transamination of fluorinated acids to amines has been reported:. Soloshonok V.A., Ohkura H., and Uneyama K. Tetrahedron Lett. 43 (2002) 5449-5452
64. Asymmetric version of the biomimetic transamination:
65. Kukhar V.P., Soloshonok V.A., Galushko S.V., and Rozhenko A.B. Dokl. Akad. Nauk SSSR 310 (1990) 886-889 Chem. Abstr. 113, 78920w
66. Soloshonok V.A., and Ono T. J. Org. Chem. 62 (1997) 3030-3031
67. Soloshonok V.A., Ono T., and Soloshonok I.V. J. Org. Chem. 62 (1997) 7538-7539
68. Soloshonok V.A., Kirilenko A.G., Galushko S.V., and Kukhar V.P. Tetrahedron Lett. 35 (1994) 5063-5064
69. Soloshonok V.A., Soloshonok I.V., Kukhar V.P., and Svedas V.K. J. Org. Chem. 63 (1998) 1878-1884
70. Soloshonok V.A., Ohkura H., and Yasumoto M. J. Fluor. Chem. 127 (2006) 924-929
71. Soloshonok V.A., Ohkura H., and Yasumoto M. J. Fluor. Chem. 127 (2006) 930-935
72. Soloshonok V.A. Angew. Chem. Int. Ed. Engl. 45 (2006) 766-769
73. Soloshonok V.A., and Berbasov D.O. J. Fluor. Chem. 127 (2006) 597-603
74. Soloshonok V.A., and Yasumoto M. J. Fluor. Chem. 128 (2007) 170-173
75. In typical experiment, a glass column (3 × 80 cm) was charged with 200 g of silica gel (hexanes). While leaving about 1 cm of the solvent on top of silica gel, a suspension of 100 g of silica gel in dichloromethane containing 1 g of DBU was charged onto the top and allowed to percolate down to the surface of silica gel. Finally, additional 100 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. Using thus prepared column, a solution [10 mol % in hexanes/acetonitrile (4/1)] of fluorinated imine 13a-f 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 14a-f (for yields, see Table 1).
76. The choice of DBU as a catalyst was based on our recent mechanistic studies:. Nagy P., Ueki H., Berbasov D.O., and Soloshonok V.A. J. Fluor. Chem. 129 (2008) 409-415