Springer Nature is making SARS-CoV-2 and COVID-19 research free. View research | View latest news | Sign up for updates

The reagent Et2AlX/CH2N2 in cyclopropanation of sterically hindered olefins, as well as oxygen- and nitrogen-containing unsaturated compounds

  • 21 Accesses

Abstract

A transition-metal-free method of cyclopropanation of sterically hindered olefins, substituted allylic alcohols, allylamines, and vinyl silyl ethers was developed using diazomethane in the presence of organic aluminum halides.

This is a preview of subscription content, log in to check access.

References

  1. 1.

    O. M. Nefedov, A. I. Ioffe, L. G. Menchikov, Khimiya karbenov [Chemistry of Carbenes], Khimiya, Moscow, 1990, 304 pp. (in Russian).

  2. 2.

    I. Marek, Z. Rappoport, A. B. Charette, in Chemistry of Organozinc Compounds. Part I, Eds Z. Rappoport, I. Marek, John Wiley & Sons, Inc., 2006, p. 1099.

  3. 3.

    I. R. Ramazanov, R. N. Kadikova, T. P. Zosim, U. M. Dzhemilev, A. de Meijere, Eur. J. Org. Chem., 2017, 7060.

  4. 4.

    I. R. Ramazanov, R. N. Kadikova, T. P. Zosim, Z. I. Nadrshina, U. M. Dzhemilev, Mendeleev Commun., 2016, 26, 434.

  5. 5.

    R. N. Kadikova, I. R. Ramazanov, T. P. P. Zosim, A. V. Yaroslavova, U. M. Dzhemilev, Tetrahedron, 2015, 71, 3290.

  6. 6.

    I. R. Ramazanov, A. V. Yaroslavova, U. M. Dzhemilev, Tetrahedron Lett., 2016, 57, 4024.

  7. 7.

    H. Hoberg, Justus Liebigs Ann. Chem., 1962, 656, 1.

  8. 8.

    I. R. Ramazanov, A. V. Yaroslavova, N. R. Yaubasarov, U. M. Dzhemilev, Russ. Chem. Bull., 2018, 67, 479.

  9. 9.

    I. R. Ramazanov, A. V. Yaroslavova, N. R. Yaubasarov, U. M. Dzhemilev, Synth. Commun., 2018, 48, 2539.

  10. 10.

    Yu. V. Tomilov, L. G. Menchikov, R. A. Novikov, O. A. Ivanova, I. V. Trushkov, Russ. Chem. Rev., 2018, 87, 201.

  11. 11.

    R. A. Novikov, D. D. Borisov, Yu. V. Tomilov, Russ. Chem. Bull., 2018, 67, 265.

  12. 12.

    E. N. Gil’manova, A. V. Yaroslavova, N. R. Yaubasarov, I. R. Ramazanov, U. M. Dzhemilev, Tez. dokl. XII Vserossiyskoi nauchnoi internet-konferentsii [Abstrs Proc. XII All-Russian Scientific Internet Conference] (Ufa, November 26–27, 2018), Izd-tvo UGNTU, 2018, p. 15 (in Russian).

  13. 13.

    T. Kippo, K. Hamaoka, I. Ryu, J. Am. Chem. Soc., 2013, 135, 632.

  14. 14.

    J. E. McMurry, M. P. Fleming, J. Org. Chem., 1976, 41, 896.

  15. 15.

    P. Cazeau, F. Duboudin, F. Moulines, O. Babot, J. Dunogues, Tetrahedron, 1987, 43, 2075.

  16. 16.

    U. M. Dzhemilev, N. R. Popod’ko, E. V. Kozlova, Metallokompleksnyi kataliz v organicheskom sinteze. Alitsiklicheskie soedineniya [Metal-Complex Catalysis in Organic Synthesis. Alicyclic Compounds], Khimiya, Moscow, 1999, 648 pp. (in Russian).

  17. 17.

    J. Barluenga, J. L. Fernandes-Simon, J. M. Concellon, M. Yus, Synthesis, 1987, 584.

  18. 18.

    J. Jiao, L. X. Nguyen, D. R. Patterson, R. A. Flowers, Org. Lett., 2007, 9, 1323.

  19. 19.

    H. Hazrati, M. Oestreich, Org. Lett., 2018, 20, 5367.

  20. 20.

    H. Sakauchi, H. Asao, T. Hasaba, S. Kuwahara, H. Kiyota, Chem. Biodivers., 2006, 3, 544.

Download references

Author information

Correspondence to I. R. Ramazanov.

Additional information

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 10, pp. 1869–1873, October, 2019.

Rights and permissions

Reprints and Permissions

About this article

Verify currency and authenticity via CrossMark

Cite this article

Ramazanov, I.R., Yaroslavova, A.V., Yaubasarov, N.R. et al. The reagent Et2AlX/CH2N2 in cyclopropanation of sterically hindered olefins, as well as oxygen- and nitrogen-containing unsaturated compounds. Russ Chem Bull 68, 1869–1873 (2019). https://doi.org/10.1007/s11172-019-2638-5

Download citation

Key words

  • organoaluminum compounds
  • diazomethane
  • aluminum carbenoids
  • cyclopropanation