Abstract
Mono- and disubstituted aziridines derived from sterically hindered olefins of the adamantane series are synthesized. The opening of the aziridine ring under the action of acids is quite a regio- and stereoselective process. Depending on the nature of the nucleophilic agent, the opening of the 2,2-disubstituted aziridine ring can occur by the SN1 or SN2 mechanism.
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Sweeney, J.B., Chem. Soc. Rev., 2002, vol. 31, p. 247.
McCoull, W. and Davis, F.A., Synthesis, 2000, vol. 10, p. 1347.
Hu, X.E., Tetrahedron, 2004, vol. 60, p. 2701.
Aziridines and Epoxides in Organic Synthesis, Yudin, A.K., Ed., Weinheim: Wiley, 2006.
Chai, Z., Yang, P.-J., Zhang, H., Wang, S., and Yang, G., Angew. Chem., Int. Ed., 2017, vol. 56, p. 650.
Shiomi, N., Kuroda, M., and Nakamura, S., Chem. Commun., 2017, vol. 53, p. 1817.
Luginina, J. and Turks, M., Chem. Heterocycl. Compd., 2016, vol. 52, p. 773.
Li, D., Yang, D., Wang, L., Liu, X., Jiang, X., and Wang, R., Chem. Eur. J., 2016, vol. 22, p. 17141.
Craig, R.A., O’Connor, N.R., Goldberg, A.F.G., and Stoltz, B.M., Chem. Eur. J., 2014, vol. 20, p. 4806.
Fernández-Megía, E.A., Montaos, M.A., and Sardina, F.J., J. Org. Chem., 2000, vol. 65, p. 6780.
Hodgkinson, T.J. and Shipman, M., Tetrahedron, 2001, vol. 57, p. 4467.
Katoh, T., Itoh, E., Yoshino, T., and Terashima, S., Tetrahedron, 1997, vol. 53, p. 10229.
Coleman, R.S., Li, J., and Navarro, A., Angew. Chem., Int. Ed., 2001, vol. 40, p. 1736.
Gerhart, F., Higgins, W., Tardif, C., and Ducep, J.B., J. Med. Chem., 1990, vol. 33, p. 2157.
Tanner, M.E. and Miao, S., Tetrahedron Lett., 1994, vol. 35, p. 4073.
Jadhav, P.K. and Woerner, F.J., Bioorg. Med. Chem. Lett., 1992, vol. 2, p. 353.
Chakraborty, T. and Gangakhedkar, K.K., Tetrahedron Lett., 1991, vol. 32, p. 1897.
Kolocouris, N., Zoidis, G., Foscolos, G.B., Fytas, G., Prathalingham, R., Kelly, J.M., Naesens, L., and De Clercq, E. Bioorg. Med. Chem. Lett., 2007, vol. 17, p. 4358. doi https://doi.org/10.1016/j.bmcl.2007.04.108
Zoidis, G., Fytas, C., Papanastasiou, I., Foscolos, G. B., Fytas, G., Padalko, E., Clercq, E.D., Naesens, L., Neyts, J., and Kolocouris, N., Bioorg. Med. Chem., 2006, vol. 14, p. 3341. doi https://doi.org/10.1016/j.bmc.2005.12.056
Wanka, L., Iqbal, K., and Schreiner, P.R., Chem. Rev., 2013, vol. 113, p. 3516.
Zoidis, G., Tsotinis, A., Kolocouris, N., Kelly, J.M., Prathalingam, S.R., Naesens, L., and De Clercq, E., Org. Biomol. Chem., 2008, vol. 6, p. 3177.
Klimochkin, Yu.N., Shiryaev, V.A., and Leonova, M.V., Russ. Chem. Bull., 2015, vol. 64, p. 1473. doi https://doi.org/10.1007/s11172-015-1035-y
Olah, G.A., Wu, A.H., and Farooq, O., J. Org.Chem., 1989, vol. 54, p. 1452.
Leonova, M.B., Baimuratov, M.R., and Klimochkin, Yu.N., Russ. J. Org. Chem., 2015, vol. 51, p. 26. doi https://doi.org/10.1134/S1070428015010054
Baimuratov, M.R., Leonova, M.V., Rybakov, V.B., and Klimochkin, Yu.N., Chem. Heterocycl. Compd., 2015, vol. 51, p. 582. doi https://doi.org/10.1007/s10593-015-1740-3
Buckley, B.R., Patel, A.P., and Wijayantha, K.G.U., J. Org. Chem., 2013, vol. 78, p. 1289.
Kelly, J.W., Eskew, N.L., and Evans, S.A., J. Org. Chem., 1986, vol. 51, p. 95.
Sasaki, T., Eguchi, S., and Hirako, Y., Tetrahedron, 1976, vol. 32, p. 437.
Van Ende, D. and Krief, A., Angew. Chem., Int. Ed., 1974, vol. 13, p. 279.
Cage Hydrocarbons, Olah, G.A., Ed., New York: Wiley, 1990.
Schreiner, P.R., Chernish, L.V., Gunchenko, P.A., Tikhonchuk, E.Yu., Hausmann, H., Serafin, M., Schlecht, S., Dahl, J.E.P., Carlson, R.M.K., and Fokin, A.A., Nature, 2011, vol. 477, p. 308.
Valiulin, R.A., Mamidyala, S., and Finn, M.G., J. Org. Chem., 2015, vol. 80, p. 2740.
Harnying, W., Kitisriworaphan, W., Pohmakotr, M., and Enders, D., Synlett., 2007, vol. 16, p. 2529. doi https://doi.org/10.1055/s-2007-986642
Kitamura, M., Hirokawa, Y., and Maezaki, N., Chem. Eur. J., 2009, vol. 15, p. 9911. doi https://doi.org/10.1002/chem.200901212
Leonova, M.V., Baimuratov, M.R., and Klimochkin, Yu.N., Russ. J. Org. Chem., 2017, vol. 53, p. 326. doi https://doi.org/10.1134/S1070428017030034
Leonova, M.V., Baimuratov, M.R., and Klimochkin, Yu.N., Russ. J. Org. Chem., 2014, vol. 50, p. 1268. doi https://doi.org/10.1134/S107042801409005X
Kline, M. and Cheatham, S., Magn. Res. Chem., 2003, vol. 41, p. 307.
Alabugin, I.V., Stereoelectronic Effects: a Bridge Between Structure and Reactivity, New York: Wiley, 2016.
Breuer, E., Somekh, L., and Ringel, I., Org. Magn. Res., 1977, vol. 9, p. 328. doi https://doi.org/10.1002/mrc.1270090609
Brois, S.J. and Beardsley, G.P., Tetrahedron Lett., 1966, vol. 42, p. 5113. doi https://doi.org/10.1016/S0040-4039(01)89289-3
Okoromoba, O.E., Li, Z., Robertson, N., Mashuta, M.S., Couto, U.R., Tormena, C.F., Xu, B., and Hammond, G.B., Chem. Commun., 2016, vol. 52, p. 13353. doi https://doi.org/10.1039/C6CC07855A
Alvernhe, G.M., Ennakoua, C.M., Lacombe, S.M., and Laurent, A.J., J. Org. Chem., 1981, vol. 46, p. 4938. doi https://doi.org/10.1021/jo00337a024
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Original Russian Text © M.V. Leonova, N.V. Belaya, M.R. Baimuratov, Yu.N. Klimochkin, 2018, published in Zhurnal Organicheskoi Khimii, 2018, Vol. 54, No. 11, pp. 1642–1648.
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Leonova, M.V., Belaya, N.V., Baimuratov, M.R. et al. Synthesis and Transformations of 2-(Adamantan-1-yl)aziridine. Russ J Org Chem 54, 1643–1651 (2018). https://doi.org/10.1134/S1070428018110040
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DOI: https://doi.org/10.1134/S1070428018110040