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Synthesis of chiral multifunctional N-terpene-containing amino acid derivatives based on simplest achiral amino acids and natural monoterpenes

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Abstract

N-Terpene-containing amino acid derivatives were synthesized by the reaction of dimeric nitroso chlorides, which were prepared from 3-carene, α-pinene, and limonene, with simplest amino acids or their esters. In the case of 3-carene and α-pinene, the corresponding adducts are formed stereospecifically.

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References

  1. P. A. Petukhov, S. N. Bizyaev, A. V. Tkachev, Russ. Chem. Bull. (Int. Ed.), 2001, 50, 2106 [Izv. Akad. Nauk, Ser. Khim., 2001, 2013].

    Article  CAS  Google Scholar 

  2. N. B. Gorshkov, A. M. Agafontsev, A. V. Tkachev, Russ. Chem. Bull. (Int. Ed.), 2010, 59, 1467 [Izv. Akad. Nauk, Ser. Khim., 2010, 1434].

    Article  CAS  Google Scholar 

  3. S. N. Bizjaev, T. V. Rybalova, Yu. V. Gatilov, A. V. Tkachev, Mendeleev Commun., 2004, 14(1), 18.

    Article  Google Scholar 

  4. S. N. Bizyaev, A. V. Tkachev, Russ. Chem. Bull. (Int. Ed.), 2012, 61, 589 [Izv. Akad. Nauk, Ser. Khim., 2012, 587].

    Article  CAS  Google Scholar 

  5. S. V. Larionov, A. V. Tkachev, Ross. Khim. Zh., 2004, 48 154 [Mendeleev Chem. J. (Engl. Transl.), 2004, 48]

    CAS  Google Scholar 

  6. Z. A. Savel’eva, A. V. Tkachev, L. A. Glinskaya, S. N. Bizyaev, R. F. Klevtsova, S. V. Larionov, Russ. J. Coord. Chem. (Engl. Transl.), 2009, 35, 128 [Koord. Khim., 2009, 35, 130]

    Article  Google Scholar 

  7. S. V. Larionov, L. I. Myachina, L. A. Glinskaya, R. F. Klevtsova, E. G. Boguslavskii, A. M. Agafontsev, A. V. Tkachev, Russ. J. Coord. Chem., 2010, 36, 579 [Koord. Khim., 2010, 36, 583]

    Article  CAS  Google Scholar 

  8. S. V. Larionov, A. V. Tkachev, L. I. Myachina, Z. A. Savel’eva, L. A. Glinskaya, R. F. Klevtsova, A. M. Agafontsev, S. N. Bizyaev, Russ. J. Coord. Chem. (Engl. Transl.), 2009, 35, 286 [Koord. Khim., 2009, 35, 291]

    Article  CAS  Google Scholar 

  9. T. E. Kokina, R. F. Klevtsova, L. A. Glinskaya, A. M. Agafontsev, A. V. Tkachev, S. V. Larionov, Russ. J. Inorg. Chem. (Engl. Transl.), 2008, 53, 696 [Zh. Neorg. Khim., 2008, 53, 758].

    Article  Google Scholar 

  10. S. E. Denmark, Yu. Fan, Tetrahedron: Asymmetry, 2006, 17, 687

    Article  CAS  Google Scholar 

  11. A. V. Malkov, M. Bell, F. Castelluzzo, P. Kočovský, Org. Lett., 2005, 7, 3219

    Article  CAS  Google Scholar 

  12. A. V. Malkov, M. Orsini, D. Pernazza, K. W. Muir, V. Langer, P. Meghani, P. Kočovský, Org. Lett., 2002, 4, 1047

    Article  CAS  Google Scholar 

  13. A. V. Malkov, P. Kočovský, Eur. J. Org. Chem., 2007, 1, 29

    Article  Google Scholar 

  14. M. Leven, N. Schlörer, J.-M. Neudörfl, B. Goldfuss, Chem. Eur. J., 2010, 16, 13443

    Article  CAS  Google Scholar 

  15. O. Mamula, A. von Zelewsky, Coord. Chem. Rev., 2003, 242, 87.

    Article  CAS  Google Scholar 

  16. G. De. Santis, L. Fabbrizzi, M. Licchelli, C. Mangano, D. Sacchi, N. Sardone, Inorg. Chim. Acta, 1997, 257, 69.

    Article  Google Scholar 

  17. A. R. Fakhari, M. R. Ganjali, M. Shamsipur, Anal. Chem., 1997, 69, 3693.

    Article  CAS  Google Scholar 

  18. J. R. Dilworth, N. Wheatley, Coord. Chem. Rev., 2000, 199, 89.

    Article  CAS  Google Scholar 

  19. I. A. Fallis, Annu. Rep. Prog. Chem. Sect. A., 2002, 98, 321.

    Article  CAS  Google Scholar 

  20. A. V. Tkachev, Ros. Khim. Zh., (Zh. Vsesoyuz. Khim. Obshch. im. D. I. Mendeleeva), 1998, 42 No. 1–2, 42 [Mendeleev Chem. J. (Engl. Transl.), 1998, 42 No. 1–2].

    CAS  Google Scholar 

  21. A. V. Tkachev, A. Yu. Denisov, A. V. Rukavishnikov, A. M. Chibirjaev, Yu. V. Gatilov, I. Yu. Bagrjanskaja, Aust. J. Chem., 1992, 45, 1077.

    Article  CAS  Google Scholar 

  22. S. A. Bakunov, A. Yu. Denisov, A. V. Tkachev, Tetrahedron, 1995, 51(31), 8565.

    Article  CAS  Google Scholar 

  23. S. V. Larionov, T. E. Kokina, A. M. Agafontsev, K. S. Marenin, L. A. Glinskaya, I. V. Korol’kov, M. I. Rakhmanova, E. M. Uskov, P. E. Plyusnin, A. V. Tkachev, Russ. Chem. Bull. (Int. Ed.), 2011, 60, 2555 [Izv. Akad. Nauk, Ser. Khim., 2011, 2506].

    Article  CAS  Google Scholar 

  24. L. F. Tietze, T. Eicher, Reaktionen und Synthesen im organisch-chemischen Praktikum und Forschungslaboratorium, 2nd ed, Georg Thieme Verlag, Stuttgart, 1991, Ch. 2.8, p. 135.

    Book  Google Scholar 

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Correspondence to A. V. Tkachev.

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Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 3, pp. 0759–0764, March, 2014.

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Marenin, K.S., Agafontsev, A.M. & Tkachev, A.V. Synthesis of chiral multifunctional N-terpene-containing amino acid derivatives based on simplest achiral amino acids and natural monoterpenes. Russ Chem Bull 63, 759–764 (2014). https://doi.org/10.1007/s11172-014-0504-z

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  • DOI: https://doi.org/10.1007/s11172-014-0504-z

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