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Intramolecular cyclization of acetylene-containing α-amino carboxylates and α-amino phosphonates: synthesis of α-CF3-substituted dehydroprolines and their P-analogs

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Abstract

CF3-Containing α-arylpropargyl-α-amino carboxylates and α-arylpropargyl-α-amino phosphonates on treatment with the Brønsted or Lewis acids undergo cyclization involving the free NH2 group and triple bond to yield the corresponding dehydroprolines and their phosphorus analogs.

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References

  1. J. R. Del Valle, M. Goodman, J. Org. Chem., 2003, 68, 3923

    Article  Google Scholar 

  2. N. Pellegrini, M. Schmitt, J.-J. Bourguignon, Tetrahedron Lett., 2003, 44, 6779

    Article  CAS  Google Scholar 

  3. J. Zhang, W. Wang, C. Xiong, V. J. Hruby, Tetrahedron Lett., 2003, 44, 1413

    Article  CAS  Google Scholar 

  4. J. R. Del Valle, M. Goodman, Angew. Chem., Int. Ed., 2002, 41, 1600

    Article  Google Scholar 

  5. Q. Xia, B. Ganem, Tetrahedron Lett., 2002, 43, 1597

    Article  CAS  Google Scholar 

  6. C. Flamant-Robin, Q. Wian, A. Chiaroni, N. A. Sasaki, Tetrahedron Lett., 2002, 43, 10475

    Google Scholar 

  7. M. Nevalainen, P. M. Kauppinen, A. M. P. Koskinen, J. Org. Chem., 2001, 66, 2061

    Article  CAS  Google Scholar 

  8. T. M. Kamenecka, Y.-J. Park, L. S. Lin, T. Jr. Lanza, W. K. Hagmann, Tetrahedron Lett., 2001, 42, 8571

    Article  CAS  Google Scholar 

  9. H. Wu, Y.-P. He, L.-Z. Gonga, Adv. Synth. Catal., 2012, 354, 975.

    Article  CAS  Google Scholar 

  10. D. Damour, F. Herman, R. Labaudinie`re, G. Pantel, M. Vuilhorgne, S. Mignani, Tetrahedron, 1999, 55, 10135

    Article  CAS  Google Scholar 

  11. K. K. Schumacher, J. Jiang, M. M. Joullié, Tetrahedron: Asymmetry, 1998, 9, 47.

    CAS  Google Scholar 

  12. Y. Xu, J. Choi, M. I. Calaza, S. Turner, H. Rapoport, J. Org. Chem., 1999, 64, 4069

    Article  CAS  Google Scholar 

  13. M.-C. Fournie-Zaluski, P. Coric, V. Thery, W. Gonzalez, H. Meudal, S. Turcaud, J.-B. Michel, B. P. Roques, J. Med. Chem., 1996, 39, 2594

    Article  CAS  Google Scholar 

  14. E. Kato, K. Yamamoto, Y. Kawashima, T. Watanabe, M. Oya, T. Iso, J. Iwao, Chem. Pharm. Bull., 1985, 33, 4836

    Article  CAS  Google Scholar 

  15. F. Manfré, J. P. Pulicani, Tetrahedron: Asymmetry, 1994, 5, 235.

    Google Scholar 

  16. N. Sewald, K. Burger, Synthesis of Fluoro-Containing Amino Acids, Eds V. P. Kukhar, V. A. Soloshonok, John Wiley and Sons Ltd., New York-Brisbane-Toronto, 1995

  17. K. Burger, K. Muetze, W. Hollweck, B. Koksch, Tetrahedron, 1998, 54, 5915

    Article  CAS  Google Scholar 

  18. A. Sutherland, C. L. Willis, Nat. Prod. Rep., 2000, 621

    Google Scholar 

  19. B. Koksch, N. Sewald, H.-J. Hofmann, K. Burger, H.-D. Jakubke, J. Pept. Sci., 1997, 3, 157

    Article  CAS  Google Scholar 

  20. J.-C. Horng, D. P. Raleigh, J. Am. Chem. Soc., 2003, 125, 9286

    Article  CAS  Google Scholar 

  21. R. E. Banks, J. C. Taltow, B. E. Smart, Organofluorine Chemistry: Principles and Commercial Applications, Plenum Press, New York, 1994

    Book  Google Scholar 

  22. P. Wang, Y. Tang, D. A. Tirrell, J. Am. Chem. Soc., 2003, 125, 6900

    Article  CAS  Google Scholar 

  23. E. Carosati, S. Sciabola, G. Cruciani, J. Med. Chem., 2004, 47, 5114.

    Article  CAS  Google Scholar 

  24. G. T. Shchetnikov, M. A. Zotova, C. Bruneau, P. H. Dixneuf, S. N. Osipov, Eur. J. Org. Chem., 2010, 1587.

    Google Scholar 

  25. M. A. Zotova, T. P. Vasilyeva, A. S. Peregudov, S. N. Osipov, J. Fluorine Chem., 2012, 135, 33.

    Article  CAS  Google Scholar 

  26. B. C. J. van Esseveldt, P. W. H. Vervoort, F. L. van Delft, F. P. J. T. Rutjes, J. Org. Chem., 2005, 70, 1791

    Article  Google Scholar 

  27. H. Wu, Y.-P. He, L.-Z. Gonga, Adv. Synth. Catal., 2012, 354, 975

    Article  CAS  Google Scholar 

  28. B. C. J. van Esseveldt, F. L. van Delft, R. de Gelder, F. P. J. T. Rutjes, Org. Lett., 2003, 5, 1717.

    Article  Google Scholar 

  29. P. Kafarski, B. Lejczak, Curr. Med. Chem. Anticancer Agents, 2001, 1, 301

    Article  CAS  Google Scholar 

  30. J. Grembecka, P. Kafarski, Mini Rev. Med. Chem., 2001, 1, 133

    Article  CAS  Google Scholar 

  31. F. R. Atherton, C. H. Hassall, R. W. Lambert, J. Med. Chem., 1986, 29, 29

    Article  CAS  Google Scholar 

  32. R. Hirschmann, A. B. Smith, C. M. Taylor, III., P. A. Benkovic, S. D. Taylor, K. M. Yager, P. A. Sprengler, S. J. Benkovic, Science, 1994, 265, 234

    Article  CAS  Google Scholar 

  33. S. A. Dake, D. S. Raut, K. R. Kharat, R. S. Mhaske, S. U. Deshmukh, R. P. Pawar, Bioorg. Med. Chem. Lett., 2011, 21, 2527

    Article  CAS  Google Scholar 

  34. P. P. Ginnousis, P. A. Bartlett, J. Med. Chem., 1987, 301, 603

    Google Scholar 

  35. M. C. Allen, W. Fuhrer, B. Tuck, R. Wade, J. M. Wood, J. Med. Chem., 1989, 32, 1652

    Article  CAS  Google Scholar 

  36. A. Peyman, W. Stahl, K. Wagner, D. Ruppert, K.-H. Budt, Bioorg. Med. Chem. Lett., 1994, 4, 2601.

    Article  CAS  Google Scholar 

  37. D. L. Mohler, G. Shen, Org. Biomol. Chem., 2006, 4, 2082.

    Article  CAS  Google Scholar 

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Correspondence to S. N. Osipov.

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Dedicated to the Academician of the Russian Academy of Sciences I. P. Beletskaya on occassion of her anniversary.

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 3, pp. 0791–0795, March, 2013.

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Zotova, M.A., Vasil’eva, T.P. & Osipov, S.N. Intramolecular cyclization of acetylene-containing α-amino carboxylates and α-amino phosphonates: synthesis of α-CF3-substituted dehydroprolines and their P-analogs. Russ Chem Bull 62, 792–796 (2013). https://doi.org/10.1007/s11172-013-0107-0

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  • DOI: https://doi.org/10.1007/s11172-013-0107-0

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