Abstract
Nitrones cycloaddition to 1-vinyl-4,5-dihydro-1H-benzo[g]indole proceeds regio- and steroselectively affording a single diastereomer of 5-(hetaryl-substituted)isoxazolidine.
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References
Tufariello, J.J., 1,3-Dipolar Cycloaddition Chemistry, Padwa, A., Ed., New York: Wiley, 1984, vol. 2.
Jones, R.C.F., and Martin, J.N., The chemistry of heterocyclic compounds. Synthetic Application of 1,3-Dipolar Cycloaddition Chemistry Toward Heterocycles and Natural Products, Padwa, A., Pearson, W.H., Eds., New York: Wiley, 2002, vol. 59.
Grigor’ev, I.A., Nitrile Oxides, Nitrones and Nitronates in Organic Synthesis, Feuer, H., Ed., Hoboken, New Jersey: Wiley, 2007.
Pellissier, H., Tetrahedron, 2010, vol. 66, p. 8341.
Joule, J.A., Mills, K., and Smith, G.F., Heterocyclic Chemistry, Oxford: Blackwell Science, 2000.
Sobenina, L.N., Tomilin, D.N., Ushakov, I.A., Mikhaleva, A.I., Ma, J.Sh., Yang, G., and Trofimov, B.A., Synthesis, 2013, vol. 45, p. 678.
Belyaeva, K.V., Andriankova, L.V., Nikitina, L.P., Ivanov, A.V., Afonin, A.V., Ushakov, I.A., Malkina, A.G., Mikhaleva, A.I., and Trofimov, B.A., Synthesis, 2011, vol. 43, p. 2843.
Molchanov, A.P., Savinkov, R.S., Stepakov, A.V., Starova, G.L., Kostikov, R.R., Barnakova, V.S., and Ivanov, A.V., Synthesis, 2014, vol. 46, p. 771.
Tedeschi, R.J., Acetylene in Encyclopedia of Physical Science and Technology, Meyers, R.A., Ed., San Diego: Acad. Press Inc., 2001, vol. 1.
Wang, Z., Comprehensive Organic Name Reactions and Reagents. Part 3, London: Wiley, 2009, p. 2793.
Name Reactions in Heterocyclic Chemistry. II, Li, J.J., Ed., Hoboken, New Jersey: Wiley-VCH, 2011.
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Original Russian Text © A.P. Molchanov, E.V. Sirotkina, M.M. Efremova, R.R. Kostikov, A.V. Ivanov, V.S. Shcherbakova, 2015, published in Zhurnal Organicheskoi Khimii, 2015, Vol. 51, No. 5, pp. 660–662.
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Molchanov, A.P., Sirotkina, E.V., Efremova, M.M. et al. Regio- and stereoselective cycloaddition of nitrones to 1-vinyl-4,5-dihydro-1H-benzo[g]indole. Russ J Org Chem 51, 640–643 (2015). https://doi.org/10.1134/S1070428015050097
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DOI: https://doi.org/10.1134/S1070428015050097