Abstract
The asymmetric induction in the synthesis of 3,4,5-trisubstituted 4,5-dihydropyrazoles with ferrocenyl substituents, starting from the E and Z isomers of α,β-unsaturated ketones was studied. A high diastereoselectivity was revealed at the 1,2 chiral center → chiral center induction, which is independent of the configuration of the starting chalcones.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
REFERENCES
Perevalova, E.G., Reshetova, M.D., and Grandberg, K.I., Metody elementoorganicheskoi khimii: zhelezoorganicheskie soedineniya. Ferrotsen (Methods of Organoelement Chemistry: Organoiron Compounds. Ferrocene), Moscow: Nauka, 1983, pp. 160-179, 484-492.
Sokolov, V.I., Vvedenie v teoreticheskuyu stereokhimiyu (Introduction into Theoretical Stereochemistry), Moscow: Nauka, 1979, pp. 120-132.
Hayashi, T., Pure Appl. Chem., 1998, vol. 60, no. 1, pp. 7-18.
Sawamura, M. and Ito, Y., Chem. Rev., 1992, vol. 92, no. 5, pp. 857-871.
Spencer, J., Cramlich, V., Hausel, R., and Togni, A., Tetrahedron: Asymmetry, 1996, vol. 7, no. 1, pp. 41-47.
Marquarding, D., Klusacek, H., Gokel, G., and Ugi, I., J. Am. Chem. Soc., 1970, vol. 92, no. 18, pp. 5389-5396.
Battele, L.F., Bau, R., Gokel, G., and Ugi, I., J. Am. Chem. Soc., 1973, vol. 95, no. 2, pp. 482-486.
Urban, R. and Ugi, I., Angew. Chem. Int. Ed. Engl., 1975, vol. 14, no. 1, pp. 61-65.
Urban, R., Eberle, G., Marquarding, D., and Ugi, I., Angew. Chem. Int. Ed. Engl., 1976, vol. 15, no. 10, pp. 627-635.
Klimova, E.I., Postnov, V.N., Meleshonkova, N.N., Zaks, A.S., and Yushkov, V.V., Khim.-Farm. Zh., 1992, vol. 26, no. 7, pp. 69-72.
Klimova, E.I., Postnov, V.N., Meleshonkova, N.N., Zaks, A.S., and Chukichev, E.M., Khim.-Farm. Zh., 1992, vol. 26, no. 7, pp. 34-39.
Klimova, E.I., Postnov, V.N., Meleshonkova, N.N., Martines Garsia, M., and Zaks, A.S., Khim.-Farm. Zh., 1994, vol. 28, no. 6, pp. 33-35.
Klimova, E.I., Ruiz Ramirez, L., Martines Garsia, M., Espinosa, R.G., and Meleshonkova, N.N., Izv. Ross. Akad. Nauk, Ser. Khim., 1996, no. 11, pp. 2743-2752.
Postnov, V.N., Andrianov, V.G., Struchkov, Yu.T., Baran, A.M., and Sazonova, V.A., J. Organomet. Chem., 1984, vol. 262, no. 2, pp. 201-208.
Klimova, E.I., Martines Garsia, M., Klimova-Berestneva, T., Ruiz Ramirez, L., Al'vares Toledano, S., and Toskano, R.A., Izv. Ross. Akad. Nauk., Ser. Khim., 1999, no. 4, pp. 765-774.
Klimova, E.I., Martinez Garcia, M., Klimova Berestneva, T., Alvarez, C.T., Toskano, R.A., and Ruiz Ramirez, L., J. Organomet. Chem., 1999, vol. 585, no. 2, pp. 106-112.
Postnov, V.N., Klimova, E.I., Martinez Garcia, M., Meleshonkova, N.N., Rybakov, V.V., and Aslanov, L.A., J. Organomet. Chem., 1994, vol. 476, no. 1, pp. 189-196.
Warawa, E.J. and Campbell, J.R., J. Org. Chem., 1974, vol. 39, no. 24, pp. 3511-3519.
Klimova, E.I., Ruiz Ramirez, L., Klimova, T., and Martinez Garcia, M., J. Organomet. Chem., 1998, vol. 559, no. 1, pp. 43-49.
Klimova, E.I., Klimova, T., Martinez Garcia, M., and Meleshonkova, N.N., Mendeleev Commun., 1997, no. 6, pp. 233-235.
Author information
Authors and Affiliations
Rights and permissions
About this article
Cite this article
Klimova-Berestneva, T., Martinez Garcia, M., Meleshonkova, N.N. et al. Asymmetric Induction in the Synthesis of 3,4,5-Trisubstituted Ferrocenyl-4,5-dihydropyrazoles. Russian Journal of General Chemistry 71, 1626–1631 (2001). https://doi.org/10.1023/A:1013975608976
Issue Date:
DOI: https://doi.org/10.1023/A:1013975608976