Operationally convenient asymmetric synthesis of (S)- and (R)-3-amino-4,4,4-trifluorobutanoic acid. Part I: Enantioselective biomimetic transamination of isopropyl 4,4,4-trifluoro-3-oxo-butanoate

Journal of Fluorine Chemistry

Volumn 127, Issue 7, 2006, Pages 924-929

  Soloshonok, Vadim A ^a   Ohkura, Hironari ^a   Yasumoto, Manabu ^a  

^a UNIVERSITY OF OKLAHOMA   (United States)

Author keywords

1,3 Proton shift reaction; Asymmetric synthesis; Biomimetic reductive methodology; Enamines; Fluorine and compounds; Imines; Operationally convenient conditions

Indexed keywords

EID: 33745200248     PISSN: 00221139     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jfluchem.2006.04.003     Document Type: Article

References (47)

1. In: Juaristi E.C., and Soloshonok V.A. (Eds). Enantioselective Synthesis of β-Amino Acids (2005), Wiley-VCH Ltd.
2. Seebach D., Hook D.F., and Glattli A. Biopolymers 84 (2006) 23-37
3. Cheng R.P., Gellman S.H., and DeGrado W.F. Chem. Rev. 101 (2001) 3219-3232
4. In: Kukhar V.P., and Soloshonok V.A. (Eds). Fluorine-Containing Amino Acids. Synthesis and properties (1994), John Wiley and Sons Ltd., Chichester
5. In: Ojima I., McCarthy J.R., and Welch J.T. (Eds). Biomedical Frontiers of Fluorine Chemistry, ACS Books (1996), American Chemical Society, Washington, DC
6. In: Soloshonok V.A. (Ed). Enantiocontrolled Synthesis of Fluoro-Organic Compounds: Stereochemical Challenges and Biomedicinal Targets (1999), Wiley, Chichester
7. In: Soloshonok V.A. (Ed). ACS Symposium Series #911. Oxford University Press (2005)
8. For pioneering works in this area by Professor Seebach, see:
9. Mathad R.I., Gessier F., Seebach D., and Jaun B. Helv. Chim. Acta 88 (2005) 266-280
10. Hook D.F., Gessier F., Noti C., Kast P., and Seebach D. Chem. Biol. Chem. 5 (2004) 691-706
11. Gessier F., Noti C., Rueping M., and Seebach D. Helv. Chim. Acta 86 (2003) 1862-1870
12. For recent review on asymmetric synthesis of fluorinated β-amino acids, see:. Fustero S., Sanz-Cervera J.F., and Soloshonok V.A. In: Juaristi E.C., and Soloshonok V.A. (Eds). Enantioselective Synthesis of β-Amino Acids. second ed. (2005), Wiley-VCH Ltd.
13. Soloshonok V.A., Ohkura H., Sorochinsky A., Voloshin N., Markovsky A., Belik M., and Yamazaki T. Tetrahedron Lett. 43 (2002) 5445-5448
14. Sorochinsky A., Voloshin N., Markovsky A., Belik M., Yasuda N., Uekusa H., Ono T., Berbasov D.O., and Soloshonok V.A. J. Org. Chem. 68 (2003) 7448-7454
15. For short communication on this project, see:. Soloshonok V.A., Ono T., and Soloshonok I.V. J. Org. Chem. 62 (1997) 7538-7539
16. For biomimetic transamination of aldehydes and ketones, see:
17. Soloshonok V.A., Kirilenko A.G., Kukhar V.P., and Resnati G. Tetrahedron Lett. 35 (1994) 3119-3122
18. Ono T., Kukhar V.P., and Soloshonok V.A. J. Org. Chem. 61 (1996) 6563-6569
19. Soloshonok V.A., and Ono T. Tetrahedron 52 (1996) 14701-14712
20. Soloshonok V.A., and Ono T. J. Org. Chem. 62 (1997) 3030-3031
21. For biomimetic transamination of α- and β-keto carboxylic acid derivatives, see:
22. Soloshonok V.A., and Kukhar V.P. Tetrahedron 52 (1996) 6953-6964
23. Soloshonok V.A., and Kukhar V.P. Tetrahedron 53 (1997) 8307-8314
24. Soloshonok V.A., Soloshonok I.V., Kukhar V.P., and Svedas V.K. J. Org. Chem. 63 (1998) 1878-1884
25. see also Refs. [7,8a].
26. For new, double biomimetic transamination of carboxylic acids to the corresponding amines, see:. Soloshonok V.A., Ohkura H., and Uneyama K. Tetrahedron Lett. 43 (2002) 5449-5452
27. The term "transamination" was coined in the following paper. Braunshtein A.E., and Kritsman M.G. Biokhimiya (Moscow) 2 (1937) 859-874
28. Soloshonok V.A., and Berbasov D.O. J. Fluor. Chem. 125 (2004) 1757-1763
29. Upthagrove A.L., and Nelson W.L. Drug Metab. Dispos. 29 (2001) 1377-1388
30. Jiang J., Shah H., and DeVita R. J. Org. Lett. 5 (2003) 4101-4103
31. Yuan C., Li S., Xiao J., Cui S., and Wang G. Phosphorus Sulfur Silicon Relat. Elem. 177 (2002) 1731-1734
32. Yuan C., Li S., and Xiao J. Heteroatom. Chem. 11 (2000) 541-545
33. Xiao J., Zhang X., and Yuan C. Heteroatom. Chem. 11 (2000) 536-540
34. R. Eisenacht, H.-P. Niedermann, D. Landau, Process for Preparing 1,1,1-Trifluoro-2-aminoalkanes from Imines American Cyanamid C. USA. U.S. 2000; US 6166259 A 20001226; Application: US 2000-537196 20000328. Priority: US 99-129460.
35. Ohkura H., Berbasov D.O., and Soloshonok V.A. Tetrahedron 59 (2003) 1647-1656
36. Khotkevich A.B., Soloshonok V.A., and Yagupolskii Y.L. Zh. Obshch. Khim. 60 (1990) 1005-1008 (Chemistry Abstract 113: 171274y)
37. For our discussions on this subject see the following papers and references in them:
38. Soloshonok V.A., Kukhar V.P., Galushko S.V., Svistunova N.Y., Avilov D.V., Kuzmina N.A., Raevski N.I., Struchkov Y.T., Pisarevsky A.P., and Belokon Y.N. J. Chem. Soc. Perkin Trans. 1 (1993) 3143-3155
39. Soloshonok V.A., Hayashi T., Ishikawa K., and Nagashima N. Tetrahedron Lett. 35 (1994) 1055-1058
40. Soloshonok V.A., Avilov D.V., and Kukhar V.P. Tetrahedron 52 (1996) 12433-12442
41. Soloshonok V.A., Kacharov A.D., Avilov D.V., and Hayashi T. Tetrahedron Lett. 37 (1996) 7845-7848
42. Soloshonok V.A., Kacharov A.D., Avilov D.V., Ishikawa K., Nagashima N., and Hayashi T. J. Org. Chem. 62 (1997) 3470-3479
43. This is an exact quotation from one of the critique the corresponding author has received on his NHI proposal.
44. Kanai M., Yasumoto M., Kuriyama Y., Inomiya K., Katsuhara Y., Higashiyama K., and Ishii A. Org. Lett. 5 (2003) 1007-1010
45. Consider the fact that in two out of three conformations this group can act as a methyl group.
46. Soloshonok V.A. Angew. Chem. In. Ed. Engl. 45 (2006) 766-769
47. Soloshonok V.A., and Berbasov D.O. J. Fluor. Chem. 127 (2006) 597-603