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Asymmetric Diels-Alder reaction between acrylates and cyclopentadiene in the presence of chiral catalysts

  • Organic Synthesis and Industrial Organic Chemistry
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Abstract

Asymmetric Diels-Alder reaction between cyclopentadiene and alkyl and cycloalkyl acrylates in the presence of new chiral catalysts, BBr3·MentOEt, AlCl2OMent, BBr2OMent, and BBr(OMent)2, was studied. Optically active bicyclo[2.2.1]hept-2-ene-5-carboxylates were synthesized. The influence of the reaction conditions on the total and optical yields and on the stereoselectivity of the adducts synthesized was examined.

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References

  1. Pavlov, V.A., Usp. Khim., 2004, vol. 42, no. 12, pp. 1269–1304.

    Google Scholar 

  2. Murzin, D.Yu., Myaki-Arvela, P., and Salmi, T., Kinet. Katal., 2003, vol. 44, no. 3, pp. 353–364.

    Article  Google Scholar 

  3. Stinson, S.C., Chem. Eng. News, 1999, no. 1, pp. 101–106.

  4. Gavrilov, K.N., Bondarev, O.G., and Polosukhin, A.I., Usp. Khim., 2004, vol. 73, no. 7, pp. 726–756.

    Google Scholar 

  5. Potapov, V.M., Stereokhimiya (Stereochemistry), Moscow: Khimiya, 1988.

    Google Scholar 

  6. Kas’yan, L.I., Okovityi, S.I., Bombushkar’, M.F., et al., Zh. Org. Khim., 2000, vol. 36, no. 2, pp. 218–228

    Google Scholar 

  7. Kas’yan, L.I., Tarabara, I.N., Kas’yan, A.O., et al., Zh. Org. Khim., 2002, vol. 38, no. 1, pp. 29–35.

    Google Scholar 

  8. Kas’yan, A.O., Golodaeva, A.V., and Tsygankov, A.V., Zh. Org. Khim., 2002, vol. 38, no. 11, pp. 1661–1669.

    Google Scholar 

  9. Guseinov, M.M., Akhmedov, I.M., and Mamedov, E.G., Azerb. Khim. Zh., 1976, no. 1, pp. 46–48.

  10. JPN Patent 53-138926, Ref. Zh. Khim., 1981, no. 19, 19N81P.

  11. Bao, J. and Walf, D., J. Am. Chem. Soc., 1993, vol. 115, no. 9, pp. 3814–3815.

    Article  CAS  Google Scholar 

  12. Farmer, R.F., and Hamer, J., J. Org. Chem., 1966, vol. 31, no. 7, pp. 2418–2419.

    CAS  Google Scholar 

  13. Mamedov, E.G., Zh. Org. Khim., 2001, vol. 37, no. 2, pp. 230–235.

    Google Scholar 

  14. Zefirov, N.S. and Sokolov, V.I., Usp. Khim., 1967, vol. 36, no. 2, pp. 243–268.

    CAS  Google Scholar 

  15. Berson, J.A., Remaninck, A., Suzuki, S., et al., J. Amer. Chem. Soc., 1961, vol. 83, no. 8, pp. 3986–3997.

    Article  CAS  Google Scholar 

  16. Weigand-Hilgetag, Organisch-Chemische Experimentierkunst, Hilgetag, H.G. and Martini, A., Eds. Leipzig: Johann Ambrosius Barth, 1964, 3d Ed.

    Google Scholar 

  17. Akhmedov, I.M., Mamedov, E.G., Kyazimov, E.A., et al., Azerb. Khim. Zh., 1980, no. 5, p. 5155.

  18. Mamedov, E.G., Azerb. Khim. Zh., 2001, no. 3, pp. 27–31.

  19. Nody, C.D., J. Amer. Chem. Soc., 1954, vol. 76, no. 11, pp. 2907–2910.

    Google Scholar 

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Original Russian Text © E.G. Mamedov, 2006, published in Zhurnal Prikladnoi Khimii, 2006, Vol. 79, No. 10, pp. 1642–1646.

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Mamedov, E.G. Asymmetric Diels-Alder reaction between acrylates and cyclopentadiene in the presence of chiral catalysts. Russ J Appl Chem 79, 1621–1625 (2006). https://doi.org/10.1134/S1070427206100120

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  • DOI: https://doi.org/10.1134/S1070427206100120

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