Abstract
Three-component reaction involving cyclopentane-1,3-dione, substituted benzaldehydes, and chloromethyl propyn(en)yl ethers results in a stereoselective formation of trans-1-aryl-2-{[prop-2-(yn)enyloxy]-methyl}spiro[2,4]hepta-4,7-diones in satisfactory yields.
References
Gopal, B., Karin, B., Patrick, J.B., Michael, L., and Peter, L., Bioorg. Med. Chem. Lett., 2006, vol. 14, p. 4694.
Frederick, R.K. Jr., Run-Ming, W., William, E.B., and Kenneth, W.B., Bioorg. Med. Chem. Lett., 1996, vol. 6, p. 1029.
McMorric, T.C., Kelner, M.J., Wang, W., Yu, J., Ectec, L.A., and Taetle, R., J. Nat. Prod., 1996, vol. 59, p.896.
Cordero, F.M., Picanecchi, F., Calvati, M., Pacchetta, V., Ollivier, J., Calaun, J., and Brandi, A., J. Org. Chem., 2003, vol. 68, p. 3271.
Boce, G. and Langer, P., Tetrahedron Lett., 2004, vol. 45, p. 3861.
Hoveyda, A.H., Evans, D.A., and Fu, G.C., Chem Rev., 1993, vol. 93, p. 1307.
Peppe, C., Chagas, R.P., and Burrow, R.A., J. Organometal. Chem., 2008, vol. 693, p. 3441.
Ren, Z., Cao, W., Ding, W., Wang, Y., and Wang, L., Synth. Commun., 2004, vol. 34, p. 3785.
Arai, S., Nakayama, K., Hatano, K., and Shioiri, T., J. Org. Chem., 1998, vol. 63, p. 9572.
Miyagawa, T., Tatenuma, T., Tadokoro, M., and Satoh, T., Tetrahedron, 2008, vol. 64, p. 5279.
Talybov, G.M., Dzhafarova, N.V., and Bairamova, S.T., Russ. J. Org. Chem., 2015, vol. 51, p. 1028. doi 10.1134/S1070428015070234
Pokonova, Yu.V., Galoidefiry (Haloesters), Moscow: Khimiya, 1966.
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Original Russian Text © G.M. Talybov, 2018, published in Zhurnal Organicheskoi Khimii, 2018, Vol. 54, No. 8, pp. 1242–1245.
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Talybov, G.M. Three-Component Stereoselective Synthesis of (1R,2S)-1-Aryl-2-{[prop-2-yn(en)yloxy]methyl}spiro[2,4]hepta-4,7-diones. Russ J Org Chem 54, 1256–1259 (2018). https://doi.org/10.1134/S1070428018080225
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DOI: https://doi.org/10.1134/S1070428018080225