Kinetics and mechanism of triethylamine-catalyzed 1,3-proton shift. Optimized and substantially improved reaction conditions for biomimetic reductive amination of fluorine-containing carbonyl compounds

Journal of Fluorine Chemistry

Volumn 129, Issue 5, 2008, Pages 409-415

  Nagy, Péter ^a   Ueki, Hisanori ^a   Berbasov, Dmitrii O ^a   Soloshonok, Vadim A ^a  

^a UNIVERSITY OF OKLAHOMA   (United States)

Author keywords

1,3 Proton shift reaction; Biomimetic reductive amination; Fluorinated compounds; Kinetics; Mechanism

Indexed keywords

EID: 42049113008     PISSN: 00221139     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jfluchem.2008.02.001     Document Type: Article

References (90)

1. The term "transamination" was coined in the following paper, A.E. Braunshtein, M.G. Kritsman, Biokhimiya (Moscow) 2 (1937) 859-874.
2. For review, see:
3. Tanner M.E. Acc. Chem. Res. 35 (2002) 237-246
4. For recent publications, see:
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. Wachtershauser G. Microbiol. Rev. 52 (1988) 452-484
10. Wachtershauser G. Prog. Biophys. Mol. Biol. 58 (1992) 85-201
11. Huber C., and Wachtershauser G. Tetrahedron Lett. 44 (2003) 1695-1697
12. Lehninger A.L., Nelson D.I., and Cox M.M. Principles of Biochemistry. 2nd ed. (1993), Worth Publishers, New York pp. 511-514
13. Toney M.D., and Kirsch J.F. Biochemistry 32 (1993) 1471-1479
14. Martell A.E. Acc. Chem. Res. 22 (1989) 115-124
15. Longenecker J.B., and Snell E.E. J. Am. Chem. Soc. 79 (1957) 142-145
16. Casella L., and Gullotti M. J. Am. Chem. Soc. 105 (1983) 803-809
17. Liu L., Rozenman M., and Breslow R. J. Am. Chem. Soc. 124 (2002) 12660-12661
18. Liu L., and Breslow R. J. Am. Chem. Soc. 124 (2002) 4978-4979
19. Breslow R., Canary J.W., Varney M., Waddell S.T., and Yang D. J. Am. Chem. Soc. 112 (1990) 5212-5219
20. Breslow R., Chmielewski J., Foley D., Johnson B., Kumabe N., Varney M., and Mehra R. Tetrahedron 44 (1988) 5515-5524
21. Jaeger D.A., Broadhurst M.D., and Cram D.J. J. Am. Chem. Soc. 101 (1979) 717-732 (and references therein on previous work reported by Cram's group)
22. For review see:
23. Layer R.W. Chem. Rev. 63 (1963) 489-510
24. Smith P.A.S., and Van Dang C. J. Org. Chem. 41 (1976) 2013-2015
25. Brandenberger H., and Cohen P.P. Helv. Chim. Acta 36 (1953) 549-554
26. For examples of synthetic application of biomimetic oxidative deamination of primary amines, see:
27. Corey E.J., and Achiwa K. J. Am. Chem. Soc. 91 (1969) 1429-1432
28. Calo V., Lopez L., and Todesco P.E. J. Perkin Trans. 1 (1972) 1652-1653
29. Ohta S., and Okamoto M. Synthesis (1982) 756-758
30. Babler J.H., and Invergo B.J. J. Org. Chem. 46 (1981) 1937-1938
31. Buckley T.F., and Rapoport H. J. Am. Chem. Soc. 104 (1982) 4446-4450
32. Baddar F.G., and Iskander Z. Nature 167 (1951) 1069-1070
33. Baddar F.G. J. Chem. Soc. (1950) 136-139
34. Baddar F.G., and Iskander Z. J. Chem. Soc. (1954) 203-209
35. Baddar F.G., and Iskander Z. J. Chem. Soc. (1954) 209-213
36. For examples of synthetic application of biomimetic reductive amination of carbonyl compounds, see:
37. Cainelli G., Giacomini D., Trere A., and Boyl P.P. J. Org. Chem. 61 (1996) 5134-5139
38. Ando M., and Kuzuhara H. Bull. Chem. Soc. Jpn. 63 (1990) 1925-1928 (references therein on previous publications)
39. Willems J.G.H., de Vries J.G., Nolte R.J.M., and Zwanenburg B. Tetrahedron Lett. 36 (1995) 3917-3920
40. Hjelmencrantz A., and Berg U. J. Org. Chem. 67 (2002) 3585-3594
41. Bachmann S., Knudsen K.R., and Jørgensen K.A. Org. Biomol. Chem. 2 (2004) 2044-2049
42. Zimmerman S., and Breslow R. J. Am. Chem. Soc. 106 (1984) 1490-1491
43. Wu Y., and Ahlberg P. J. Org. Chem. 57 (1992) 6324-6327
44. Wu Y., and Ahlberg P. Acta Chem. Scand. 46 (1992) 60-72
45. Bernauer K., Deschenaux R., and Taura T. Helv. Chim. Acta 66 (1983) 2049-2058
46. Deschenaux R., and Bernauer K. Helv. Chim. Acta 67 (1984) 373-377
47. For biomimetic transamination of fluorinated aldehydes and ketones, see:
48. Soloshonok V.A., Gerus I.L., Yagupolskii Y.I., and Kukhar V.P. Zh. Org. Khim. 23 (1987) 2308-2313
49. Soloshonok V.A., Gerus I.L., Yagupolskii Y.I., and Kukhar V.P. Chem. Abstr. 109 (1987) 55185p
50. Soloshonok V.A., Gerus I.L., Yagupolskii Y.I., and Kukhar V.P. Zh. Org. Khim. 24 (1988) 993-997
51. Soloshonok V.A., Gerus I.L., Yagupolskii Y.I., and Kukhar V.P. Chem. Abstr. 110 (1988) 134824v
52. Soloshonok V.A., Yagupolskii Y.I., and Kukhar V.P. Zh. Org. Khim. 24 (1988) 1638-1644
53. Soloshonok V.A., Yagupolskii Y.I., and Kukhar V.P. Chem. Abstr. 110 (1988) 154827b
54. Khotkevich A.B., Soloshonok V.A., and Yagupolskii Y.I. Zh. Obshch. Khim. 60 (1990) 1005-1008
55. Khotkevich A.B., Soloshonok V.A., and Yagupolskii Y.I. Chem. Abstr. 113 (1990) 171274y
56. Soloshonok V.A., Kirilenko A.G., Kukhar V.P., and Resnati G. Tetrahedron Lett. 35 (1994) 3119-3122
57. Soloshonok V.A., and Ono T. Synlett (1996) 919-921
58. Soloshonok V.A., and Ono T. Tetrahedron 52 (1996) 14701-14712
59. Ohkura H., Berbasov D.O., and Soloshonok V.A. Tetrahedron Lett. 44 (2003) 2417-2420
60. Ohkura H., Berbasov D.O., and Soloshonok V.A. Tetrahedron 59 (2003) 1647-1656
61. Berbasov D.O., Ojemaye I.D., and Soloshonok V.A. J. Fluorine Chem. 125 (2004) 603-607
62. Ono T., Kukhar V.P., and Soloshonok V.A. J. Org. Chem. 61 (1996) 6563-6569
63. Soloshonok V.A., Ohkura H., and Yasumoto M. Mendeleev Commun. (2006) 165-167
64. Soloshonok V.A., Ohkura H., and Yasumoto M. J. Fluorine Chem. 127 (2006) 708-711
65. Soloshonok V.A., and Yasumoto M. J. Fluorine Chem. 127 (2006) 889-893
66. Soloshonok V.A., and Berbasov D.O. J. Fluorine Chem. 125 (2004) 1757-1763
67. Yasumoto M., Ueki H., and Soloshonok V.A. J. Fluorine Chem. 128 (2007) 736-739
68. Soloshonok V.A., and Kukhar' V.P. Tetrahedron 53 (1997) 8307-8314 (for biomimetic transamination of fluorinated α-keto acids)
69. For biomimetic transamination of fluorinated β-keto acids, see:
70. Soloshonok V.A., Kirilenko A.G., Kukhar V.P., and Resnati G. Tetrahedron Lett. 34 (1993) 3621-3624
71. 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: Asymmetr. 5 (1994) 1119-1126
72. Soloshonok V.A., Kirilenko A.G., Fokina N.A., Galushko S.V., Kukhar V.P., Svedas V.K., and Resnati G. Tetrahedron: Asymmetr. 5 (1994) 1225-1228
73. Soloshonok V.A., and Kukhar V.P. Tetrahedron 52 (1996) 6953-6964
74. For double biomimetic transamination of fluorinated acids to amines, see:
75. Soloshonok V.A., Ohkura H., and Uneyama K. Tetrahedron Lett. 43 (2002) 5449-5452
76. For asymmetric version of the biomimetic transamination, see:
77. Kukhar V.P., Soloshonok V.A., Galushko S.V., and Rozhenko A.B. Dokl. Akad. Nauk SSSR 310 (1990) 886-889
78. Kukhar V.P., Soloshonok V.A., Galushko S.V., and Rozhenko A.B. Chem. Abstr. 113 (1990) 78920w
79. Soloshonok V.A., and Ono T. J. Org. Chem. 62 (1997) 3030-3031
80. Soloshonok V.A., Ono T., and Soloshonok I.V. J. Org. Chem. 62 (1997) 7538-7539
81. Soloshonok V.A., Kirilenko A.G., Galushko S.V., and Kukhar V.P. Tetrahedron Lett. 35 (1994) 5063-5064
82. Soloshonok V.A., Soloshonok I.V., Kukhar V.P., and Svedas V.K. J. Org. Chem. 63 (1998) 1878-1884
83. Soloshonok V.A., Ohkura H., and Yasumoto M. J. Fluorine Chem. 127 (2006) 924-929
84. Soloshonok V.A., Ohkura H., and Yasumoto M. J. Fluorine Chem. 127 (2006) 930-935
85. Soloshonok V.A. Angew. Chem. Int. Ed. Engl. 45 (2006) 766-769
86. Soloshonok V.A., and Berbasov D.O. J. Fluorine Chem. 127 (2006) 597-603
87. Soloshonok V.A., and Yasumoto M. J. Fluorine Chem. 128 (2007) 170-173
88. Jaeger D.A., and Cram D.J. J. Am. Chem. Soc. 93 (1971) 5153-5161
89. Smith S.G. J. Am. Chem. Soc. 83 (1961) 4285-4287
90. Limbach H.H., Maennle F., Detering C., and Denisov G.S. Chem. Phys. 319 (2005) 69-92