Biomimetic base-catalyzed [1,3]-proton shift reaction. A practical synthesis of β-fluoroalkyl-β-amino acids

Tetrahedron

Volumn 52, Issue 20, 1996, Pages 6953-6964

  Soloshonok, Vadim A ^a,b   Kukhar, Valery P ^b  

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

^b INSTITUTE OF BIOORGANIC CHEMISTRY AND PETROCHEMISTRY   (Ukraine)

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACID DERIVATIVE; ORGANOFLUORINE DERIVATIVE;

ARTICLE; CHIRALITY; DRUG SYNTHESIS; PRIORITY JOURNAL; REACTION ANALYSIS;

EID: 0029969511     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4020(96)00300-6     Document Type: Article

References (42)

1. Preliminary communications: (a) Soloshonok, V.A.; Kirilenko, A.G.; Kukhar, V.P.; Resnati, G. Tetrahedron Lett. 1993, 34, 3621.
2. (b) Soloshonok, V.A.; Kirilenko, A.G.; Galushko, S.V.; Kukhar, V.P. Tetrahedron Letters 1994, 35, 5063.
3. Apart from their own usually high biological activity (a-d) β-amino acids are of paramount importance in the synthesis of complex compounds such as peptides with designed conformational properties and biological functions (e-i). (a) Drey, C.N. in Chemistry and Biochemistry of the Amino Acids; B. Weinstein, Ed., Marcel Dekker, New York, 1976, vol. 4, p. 241.
4. (b) Drey, C.N. in Chemistry and Biochemistry of the Amino Acids; G.C. Barett, Ed., Chapman and Hall: New York, 1985.
5. (c) Spatola, A.F. in Chemistry and Biochemistry of the Amino Acids, Peptides and Proteins; B. Weinstein, Ed., Dekker: New York, 1983, vol. 7, p. 331.
6. (d) Griffith, O.W. Ann. Rev. Biochem. 1986, 55, 855.
7. (e) Peptide Chemistry: Design and Synthesis of Peptides, Conformational Analysis and Biological Functions. Tetrahedron-Symposia-in-Print 31, V.J. Hruby and R. Schwyzer, Eds., Tetrahedron 1988, 44, 661.
8. (f) Li, G.; Jarosinski, M.A.; Hruby, V. Tetrahedron Lett. 1993, 34, 2561.
9. (g) Giannis, A.; Kolter, T. Angew. Chem. Int. Ed. Engl. 1993, 32, 1244 .
10. (h) Paulvannan, K.; Stille, J.R. Tetrahedron Lett. 1993, 34, 8197.
11. (i) Robl, J.A.; Cimarusti, M.P.; Simpkins, L.M.; Weller, H.N.; Pan, Y.Y.; Malley, M.; DiMarco, J.D. J. Am. Chem. Soc. 1994, 116, 2348.
12. For reviews see: (a) Juaristi, E. Aldrichim. Acta 1994, 27, 3.
13. (b) Enantioselective Synthesis of β-Amino Acids, Juaristi, E. Ed.; VCH Publisher: New York, scheduled to appear in 1996.
14. For reviews see: (a) Fluorine-Containing Amino Acids: Synthesis and Properties, Kukhar, V.P.; Soloshonok, V.A., Eds.; John Wiley and Sons Publisher: Chichester, 1994.
15. (b) Kukhar, V.P.; Soloshonok, V.A. Russ. Chem. Rev. Engl. 1991, 60, 850.
16. (c) Kukhar, V.P.; Yagupolskii Yu.L.; Soloshonok, V.A. Russ. Chem. Rev. Engl. 1990, 59, 89.
17. (d) Kukhar, V.P.; Svistunova, N.Yu.; Soloshonok, V.A.; Solodenko, V.A. Russ. Chem. Rev. Engl. 1993, 62, 284.
18. Burdon, J.; McLoughlin, V. C. R. Tetrahedron 1964, 20, 2163.
19. Begue, J.-P.; Benayoud, F.; Bonnet-Delpon, D. J. Org. Chem. 1995, 60, 5029.
20. (a) Soloshonok, V.A.; Svedas, V.K.; Kukhar, V.P.; Kirilenko, A.G.; Rybakova, A.V.; Solodenko, V.A.; Fokina, N.A.; Kogut, O.V.; Galaev, I.Y.; Kozlova, E.V.; Shishkina, I.P.; Galushko, S.V. Synlett 1993, 339.
21. (b) Soloshonok, V.A.; Kirilenko, A.G.; Fokina, N.A.; Shishkina, I.P.; Galushko, S.V.; Kukhar, V.P.; Svedas, V.K.; Kozlova, E.V. Tetrahedron : Asymmetry 1994, 5, 1119.
22. (c) Soloshonok, V.A.; Fokina, N.A.; Rybakova, A.V.; Shishkina, I.P.; Galushko, S.V.; Sorochinsky, A.E.; Kukhar, V.P.; Savchenko, M.V.; Svedas, V.K. Tetrahedron : Asymmetry 1995, 6, 1601.
23. (d) Soloshonok, V.A. in Enantioselective Synthesis of β-Amino Acids, Juaristi, E. Ed.; VCH Publisher: New York, scheduled to appear in 1996.
24. For reviews: Catalytic Asymmetric Synthesis, Ojima, I., Ed.; VCH Publishers, New York, 1993.
25. Galushko, S. V.; Shishkina, I. P.; Soloshonok, V. A. J. Chromatography 1992, 592, 345.
26. (a) Walsh, C. "Enzymatic Reaction Mechanisms"; W. H. Freeman: San Francisco, 1979; pp 777-833.
27. (b) Braunstein, A.E. Enzymes, 3rd Ed. 1973, 9, 379.
28. (c) Metzler, D.E. Adv. Enzvmol. 1979, 50, 1.
29. Jaeger, D.A.; Broadhurst, M.D.; Cram, D.J. J. Am. Chem. Soc. 1979, 101, 717; and previous papers of this group cited therein.
30. Smith, P.A.S.; Dang, C.V. J. Org. Chem. 1976, 41, 2013.
31. Kuzuhara, H.; Ando, M. Bull. Chem. Soc. Jpn. 1990, 63, 1925; and papers cited therein.
32. Layer, R.W. Chem Rev. 1963, 489.
33. Hudlicky, M. Chemistry of Organic Fluorine Compounds, 2nd Ed.; E. Horwood: Chichester, 1976.
34. (a) Soloshonok, V.A.; Gerus, I.I.; Yagupolskii, Y.L.; Kukhar, V.P. Zh. Org. Khim. 1988, 24, 993; Chem. Abstr., 110: 134824v.
35. (a) Soloshonok, V.A.; Gerus, I.I.; Yagupolskii, Y.L.; Kukhar, V.P. Zh. Org. Khim. 1988, 24, 993; Chem. Abstr., 110: 134824v.
36. (b) Soloshonok, V.A.; Yagupolskii, Y.L.; Kukhar, V.P. Zh. Org. Khim. 1988, 24, 1638; Chem. Abstr., 110: 154827b.
37. (b) Soloshonok, V.A.; Yagupolskii, Y.L.; Kukhar, V.P. Zh. Org. Khim. 1988, 24, 1638; Chem. Abstr., 110: 154827b.
38. (c) Khotkevich, A.B.; Soloshonok, V.A.; Yagupolskii, Y.L. Zh. Obshch. Khim. 1990, 60, 1005; Chem. Abstr., 113: 171274y.
39. (c) Khotkevich, A.B.; Soloshonok, V.A.; Yagupolskii, Y.L. Zh. Obshch. Khim. 1990, 60, 1005; Chem. Abstr., 113: 171274y.
40. (d) Soloshonok, V.A.; Kirilenko, A.G.; Kukhar, V.P.; Resnati, G. Tetrahedron Letters 1994, 35, 3119.
41. Yagupolskii, L.M.; Il'chenko, A.Y.; Kondratenko, N.V. Russ. Chem. Rev. 1974, 43, 64.
42. 2n+1 substituted compounds, see ref. 7 and Kirmse, W.; Wonner, A.; Allen, A.D.; Tidwell, T.T. J. Am. Chem. Soc. 1992, 114, 8828.