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Aluminacyclopentanes in the synthesis of ethyl 1-hydroxycyclopentanecarboxylates

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Abstract

A one-pot procedure has been developed for the synthesis of ethyl 1-hydroxycyclopentanecarboxylates. The procedure includes cycloalumination of terminal olefins with triethylaluminum in the presence of Cp2ZrCl2, reaction of alkyl-substituted aluminacyclopentanes formed in situ with diethyl oxalate in the presence of a catalytic amount of copper salt, and acid hydrolysis.

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References

  1. Dzhemilev, U.M., Ibragimov, A.G., Zolotarev, A.P., Muslukhov, R.R., and Tolstikov, G.A., Izv. Ross. Akad. Nauk, Ser. Khim., 1989, p. 207.

  2. Dzhemilev, U.M. and Ibragimov, A.G., Usp. Khim., 2000, vol. 69, p. 134.

    Google Scholar 

  3. Dzhemilev, U.M., Ibragimov, A.G., Gilyazev, R.R., and Khafizova, L.O., Tetrahedron, 2004, vol. 60, p. 1281.

    Article  CAS  Google Scholar 

  4. Dzhemilev, U.M., Ibragimov, A.G., Zolotarev, A.P., and Tolstikov, G.A., Izv. Ross. Akad. Nauk, Ser. Khim., 1989, p. 1444.

  5. Dzhemilev, U.M., Ibragimov, A.G., Morozov, A.B., Khalilov, L.M., Muslukhov, R.R., and Tolstikov, G.A., Izv. Ross. Akad. Nauk, Ser. Khim., 1991, p. 1141.

  6. Dzhemilev, U.M., Ibragimov, A.G., Khafizova, L.O., Gilyazev, R.R., and D’yakonov, V.A., Izv. Ross. Akad. Nauk, Ser. Khim., 2004, p. 130.

  7. Plemenkov, V.V., Vvedenie v khimiyu prirodnykh soedinenii (An Introduction to the Chemistry of Natural Compounds), Kazan, 2001.

  8. Bratus, I.N., Khimiya dushistykh veshchestv (Chemistry of Fragrant Substances), Moscow: Pishchevaya Promyshlennost’, 1979.

    Google Scholar 

  9. Xiong, H. and Rieke, R.D., J. Am. Chem. Soc., 1992, vol. 114, p. 4415.

    Article  CAS  Google Scholar 

  10. Shono, T., Ishifune, M., Kinugasa, H., and Kashimura, S., J. Org. Chem., 1992, vol. 57, p. 5561.

    Article  CAS  Google Scholar 

  11. Zolotarev, A.P., Cand. Sci. (Chem.) Dissertation, Ufa, 1994.

  12. Wipf, P. and Ribe, S., Org. Lett., 2001, vol. 3, p. 1503.

    Article  CAS  Google Scholar 

  13. Dzhemilev, U.M., Ibragimov, A.G., Zolotarev, A.P., Khalilov, L.M., and Muslukhov, R.R., Izv. Ross. Akad. Nauk, Ser. Khim., 1992, p. 386.

  14. Dzhemilev, U.M., Ibragimov, A.G., Khafizova, L.O., Khalilov, L.M., Vasil’ev, Yu.V., Tuktarov, R.R., Tomilov, Yu.V., and Nefedov, O.M., Izv. Ross. Akad. Nauk, Ser. Khim., 1999, p. 572.

  15. Smith, A.B., III and Tokuyama, H., Tetrahedron, 1996, vol. 52, p. 5257.

    Article  CAS  Google Scholar 

  16. Smith, A.B., III, Strongin, R.M., Brard, L., Fursh, G.T., and Romanov, W.I., J. Am. Chem. Soc., 1993, vol. 115, p. 5829.

    Article  CAS  Google Scholar 

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Authors and Affiliations

  1. Institute of Petroleum Chemistry and Catalysis, Russian Academy of Sciences, pr. Oktyabrya 141, Ufa, 450075, Bashkortostan, Russia

    U. M. Dzhemilev, A. G. Ibragimov, L. O. Khafizova, R. R. Gilyazev & A. L. Makhamatkhanova

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  1. U. M. Dzhemilev
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  2. A. G. Ibragimov
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  3. L. O. Khafizova
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  4. R. R. Gilyazev
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  5. A. L. Makhamatkhanova
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Original Russian Text © U.M. Dzhemilev, A.G. Ibragimov, L.O. Khafizova, R.R. Gilyazev, A.L. Makhamatkhanova, 2007, published in Zhurnal Organicheskoi Khimii, 2007, Vol. 43, No. 3, pp. 352–356.

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Dzhemilev, U.M., Ibragimov, A.G., Khafizova, L.O. et al. Aluminacyclopentanes in the synthesis of ethyl 1-hydroxycyclopentanecarboxylates. Russ J Org Chem 43, 347–351 (2007). https://doi.org/10.1134/S1070428007030025

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  • DOI: https://doi.org/10.1134/S1070428007030025

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