The Effect of Substituents on the Feasibility of [1,3]-Proton Shift Reaction: New Synthetic Opportunities

Synlett

Volumn 1996, Issue 9, 1996, Pages 919-921

  Soloshonok, Vadim A ^a   Ono, Taizo ^a  

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

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0002601222     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1996-5621     Document Type: Article

References (36)

1. For general discussion of biological activity and importance of fluorinated amino compounds see monographs: (a) Biomedicinal Aspects of Fluorine Chemistry, Filler, R.; Kobayashi, Y., Eds.; Kodansha LTD: Tokyo, Elsevier Biomedicinal Press: Amsterdam - New York - Oxford, 1982. (b) Welch, J. T.; Eswarakrischnan, S. Fluorine in Bioorganic Chemistry, J. Wiley and Sons, New York, 1991. (c) Fluorine-Containing Amino Acids. Synthesis and Properties. Kukhar, V.P.; Soloshonok, V.A., Eds.; John Wiley and Sons Ltd, Chichester, 1994. For most recent publications see: (d) Fluoroorganic Chemistry: Synthetic Challenges and Biomedical Rewards; Resnati, G.; Soloshonok, V.A., Eds.; Tetrahedron Symposium-in-Print, 58; Tetrahedron 1996, 52, 1-330.
2. For general discussion of biological activity and importance of fluorinated amino compounds see monographs: (a) Biomedicinal Aspects of Fluorine Chemistry, Filler, R.; Kobayashi, Y., Eds.; Kodansha LTD: Tokyo, Elsevier Biomedicinal Press: Amsterdam - New York - Oxford, 1982. (b) Welch, J. T.; Eswarakrischnan, S. Fluorine in Bioorganic Chemistry, J. Wiley and Sons, New York, 1991. (c) Fluorine-Containing Amino Acids. Synthesis and Properties. Kukhar, V.P.; Soloshonok, V.A., Eds.; John Wiley and Sons Ltd, Chichester, 1994. For most recent publications see: (d) Fluoroorganic Chemistry: Synthetic Challenges and Biomedical Rewards; Resnati, G.; Soloshonok, V.A., Eds.; Tetrahedron Symposium-in-Print, 58; Tetrahedron 1996, 52, 1-330.
3. For general discussion of biological activity and importance of fluorinated amino compounds see monographs: (a) Biomedicinal Aspects of Fluorine Chemistry, Filler, R.; Kobayashi, Y., Eds.; Kodansha LTD: Tokyo, Elsevier Biomedicinal Press: Amsterdam - New York - Oxford, 1982. (b) Welch, J. T.; Eswarakrischnan, S. Fluorine in Bioorganic Chemistry, J. Wiley and Sons, New York, 1991. (c) Fluorine-Containing Amino Acids. Synthesis and Properties. Kukhar, V.P.; Soloshonok, V.A., Eds.; John Wiley and Sons Ltd, Chichester, 1994. For most recent publications see: (d) Fluoroorganic Chemistry: Synthetic Challenges and Biomedical Rewards; Resnati, G.; Soloshonok, V.A., Eds.; Tetrahedron Symposium-in-Print, 58; Tetrahedron 1996, 52, 1-330.
4. For general discussion of biological activity and importance of fluorinated amino compounds see monographs: (a) Biomedicinal Aspects of Fluorine Chemistry, Filler, R.; Kobayashi, Y., Eds.; Kodansha LTD: Tokyo, Elsevier Biomedicinal Press: Amsterdam - New York - Oxford, 1982. (b) Welch, J. T.; Eswarakrischnan, S. Fluorine in Bioorganic Chemistry, J. Wiley and Sons, New York, 1991. (c) Fluorine-Containing Amino Acids. Synthesis and Properties. Kukhar, V.P.; Soloshonok, V.A., Eds.; John Wiley and Sons Ltd, Chichester, 1994. For most recent publications see: (d) Fluoroorganic Chemistry: Synthetic Challenges and Biomedical Rewards; Resnati, G.; Soloshonok, V.A., Eds.; Tetrahedron Symposium-in-Print, 58; Tetrahedron 1996, 52, 1-330.
5. For general discussion of biological activity and importance of fluorinated amino compounds see monographs: (a) Biomedicinal Aspects of Fluorine Chemistry, Filler, R.; Kobayashi, Y., Eds.; Kodansha LTD: Tokyo, Elsevier Biomedicinal Press: Amsterdam - New York - Oxford, 1982. (b) Welch, J. T.; Eswarakrischnan, S. Fluorine in Bioorganic Chemistry, J. Wiley and Sons, New York, 1991. (c) Fluorine-Containing Amino Acids. Synthesis and Properties. Kukhar, V.P.; Soloshonok, V.A., Eds.; John Wiley and Sons Ltd, Chichester, 1994. For most recent publications see: (d) Fluoroorganic Chemistry: Synthetic Challenges and Biomedical Rewards; Resnati, G.; Soloshonok, V.A., Eds.; Tetrahedron Symposium-in-Print, 58; Tetrahedron 1996, 52, 1-330.
6. (a) Soloshonok, V.A.; Yagupol'skii, Yu.L.; Gerus, I.I.; Kukhar, V.P. Zh. Org. Khim. 1988, 24, 993; Chem. Abst. 1989, 110, 134824.
7. (a) Soloshonok, V.A.; Yagupol'skii, Yu.L.; Gerus, I.I.; Kukhar, V.P. Zh. Org. Khim. 1988, 24, 993; Chem. Abst. 1989, 110, 134824.
8. (b) Soloshonok, V.A.; Yagupolskii, Y.L.; Kukhar, V.P. Zh. Org. Khim. 1988, 24, 1638; Chem. Abstr. 1989, 110: 154827b.
9. (b) Soloshonok, V.A.; Yagupolskii, Y.L.; Kukhar, V.P. Zh. Org. Khim. 1988, 24, 1638; Chem. Abstr. 1989, 110: 154827b.
10. (c) Kukhar, V.P.; Soloshonok, V.A.; Galushko, S.V.; Rozhenko, A.B. Dokl. Akad. Nauk SSSR 1990, 310, 886; Chem. Abstr. 1991, 113: 78920w.
11. (c) Kukhar, V.P.; Soloshonok, V.A.; Galushko, S.V.; Rozhenko, A.B. Dokl. Akad. Nauk SSSR 1990, 310, 886; Chem. Abstr. 1991, 113: 78920w.
12. (d) Khotkevich, A.B.; Soloshonok, V.A.; Yagupolskii, Y.L. Zh. Obshch. Khim. 1990, 60, 1005; Chem. Abstr. 1991, 113: 171274y.
13. (d) Khotkevich, A.B.; Soloshonok, V.A.; Yagupolskii, Y.L. Zh. Obshch. Khim. 1990, 60, 1005; Chem. Abstr. 1991, 113: 171274y.
14. (e) Soloshonok, V.A.; Kirilenko, A.G.; Kukhar, V.P.; Resnati, G. Tetrahedron Lett. 1993, 34, 3621.
15. (f) Soloshonok, V.A.; Kirilenko, A.G.; Galushko, S.V.; Kukhar, V.P. Tetrahedron Letters 1994, 35, 5063.
16. (g) 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.
17. (h) Soloshonok, V.A.; Kirilenko, A.G.; Fokina, N.A.; Galushko, S.V.; Kukhar, V.P.; Svedas, V.K.; Resnati, G. Tetrahedron : Asymmetry 1994, 5, 1225.
18. (i) Soloshonok, V.A.; Kirilenko, A.G.; Kukhar, V.P.; Resnati, G. Tetrahedron Letters 1994, 35, 3119.
19. (j) Soloshonok, V.A.; Kukhar, V.P. Tetrahedron 1996, 52, 6953.
20. (k) Ono, T.; Kukhar, V.P.; Soloshonok, V.A. J. Org. Chem. 1996, 61, accepted for publication.
21. (a) For a review of the mechanism, see (a) Jencks, W.P. "Catalysis in Chemistry and Enzymology", McGraw-Hill, New York, N.Y., 1969, pp 143-145. For chemical modeling of the isomerization step of biological transamination, see (b) Cram, D.J.; Guthrie, R.D. J. Am. Chem. Soc. 1965, 87, 397. (c) Guthrie, R.D.; Jaeger, D.A.; Meister, W.; Cram, D.J. J. Am. Chem. Soc. 1971, 93, 5137. (d) Jaeger, D.A.; Cram, D.J. J. Am. Chem. Soc. 1971, 93, 5153.
22. (a) For a review of the mechanism, see (a) Jencks, W.P. "Catalysis in Chemistry and Enzymology", McGraw-Hill, New York, N.Y., 1969, pp 143-145. For chemical modeling of the isomerization step of biological transamination, see (b) Cram, D.J.; Guthrie, R.D. J. Am. Chem. Soc. 1965, 87, 397. (c) Guthrie, R.D.; Jaeger, D.A.; Meister, W.; Cram, D.J. J. Am. Chem. Soc. 1971, 93, 5137. (d) Jaeger, D.A.; Cram, D.J. J. Am. Chem. Soc. 1971, 93, 5153.
23. (a) For a review of the mechanism, see (a) Jencks, W.P. "Catalysis in Chemistry and Enzymology", McGraw-Hill, New York, N.Y., 1969, pp 143-145. For chemical modeling of the isomerization step of biological transamination, see (b) Cram, D.J.; Guthrie, R.D. J. Am. Chem. Soc. 1965, 87, 397. (c) Guthrie, R.D.; Jaeger, D.A.; Meister, W.; Cram, D.J. J. Am. Chem. Soc. 1971, 93, 5137. (d) Jaeger, D.A.; Cram, D.J. J. Am. Chem. Soc. 1971, 93, 5153.
24. (a) For a review of the mechanism, see (a) Jencks, W.P. "Catalysis in Chemistry and Enzymology", McGraw-Hill, New York, N.Y., 1969, pp 143-145. For chemical modeling of the isomerization step of biological transamination, see (b) Cram, D.J.; Guthrie, R.D. J. Am. Chem. Soc. 1965, 87, 397. (c) Guthrie, R.D.; Jaeger, D.A.; Meister, W.; Cram, D.J. J. Am. Chem. Soc. 1971, 93, 5137. (d) Jaeger, D.A.; Cram, D.J. J. Am. Chem. Soc. 1971, 93, 5153.
25. Benzyl trifluoromethyl ketone was prepared according to the literature procedure: Nes, W.R.; Burger, A. J. Am. Chem. Soc. 1950, 72, 5409.
26. Base-catalyzed imine-enamine isomerization is known to be much more mobile than the relative triad azomethine-azomethine prototropy. For a review, see Layer, R.W. Chem Rev. 1963, 489.
27. 2k
28. The steric effect of o-methoxy group in 1d should also be taken into account.
29. (a) Smith, P.A.S.; Dang, C.V. J. Org. Chem. 1976, 41, 2013. See also ref. 5 and
30. (b) Ingold, C.K.; Shoppee, C.W. J. Chem. Soc. 1929, 1199.
31. (c) Shoppee, C.W. J. Chem. Soc. 1931, 1225.
32. (d) Baddar, F.G. J. Chem. Soc. 1950, 136.
33. (e) Baddar, F.G.; Iskander, Z. J. Chem. Soc. 1954, 203.
34. (f) Baddar, F.G.; Iskander, Z. J. Chem. Soc. 1954, 209.
35. (g) Witkop, B.; Beiler, T.W. J. Am. Chem. Soc. 1954, 76, 5589.
36. 2, 26), 167 (33), 91 (100), 65 (16), 51 (14).