Skip to content
BY-NC-ND 3.0 license Open Access Published by De Gruyter Open Access February 21, 2014

Regio- and stereoselectivity of polar [2+3] cycloaddition reactions between (Z)-C-(3,4,5-trimethoxyphenyl)-N-methylnitrone and selected (E)-2-substituted nitroethenes

Radomir Jasiński, Magda Ziółkowska, Oleh Demchuk and Agata Maziarka
From the journal Open Chemistry

Abstract

[2+3] Cycloaddition reactions of the highly reactive (Z)-C-(3,4,5-trimethoxyphenyl)-N-methylnitrone with (E)-2-R-nitroethenes proceed under mild conditions and yield mixtures of stereoisomeric 2-methyl-3-(3,4,5-trimethoxyphenyl)-4-nitro-5-R-isoxazolidines. The effect of regiospecificity of the cycloadditions may be accounted for by the theory of electrophilicity indexes. Stereoselectivity, however, is determined by a compilation of steric and secondary orbital effects.

[1] R. Jasiński, J. Heterocyclic Chem. 50 (2013) DOI: 10.1002/jhet.2020 (in press) 10.1002/jhet.2020Search in Google Scholar

[2] T.B. Nguyen, A. Martel, C. Gaulon-Nourry, R. Dhal, G. Dujardin, Org. Prep. Proc. Int. 44, 1 (2012) http://dx.doi.org/10.1080/00304948.2012.64319310.1080/00304948.2012.643193Search in Google Scholar

[3] A. Barański, R. Jasiński, E. Cholewka, In: Z. Kowalski (Ed.), Postępy w inżynierii i technologii chemicznej (Politechnika Krakowska, Kraków, 2011) (in Polish) Search in Google Scholar

[4] A. Padwa, W.H. Pearson, Synthetic Applications of 1,3-Dipolar Cycloaddition Chemistry Toward Heterocycles and Natural Products (Wiley & Sons, Hoboken, New Jersey, 2003) 10.1002/0471221902Search in Google Scholar

[5] R. Huisgen, G. Mloston, In: A.A. Potekhin, R.R. Kostikov, M.S. Baird (Eds.), Modern Problems of Organic Chemistry (St. Petersburg University Press, St. Petersburg, 2004) Search in Google Scholar

[6] G. Chauviere, B. Bouteille, B. Enanga, C. de Albuquerque, S.L. Croft, M. Dumas, J. Périé, J. Med. Chem. 46, 270 (2003) http://dx.doi.org/10.1021/jm021030a10.1021/jm021030aSearch in Google Scholar

[7] A.F. Oleinik, K.Yu. Novitskii, E.N. Dozorova, N.P. Solov’eva, L.M. Polukhina, N.A. Novitskaya, G. N. Pershin, Pharm. Chem. J. 14, 610 (1980) http://dx.doi.org/10.1007/BF0115637210.1007/BF01156372Search in Google Scholar

[8] M.A. Iradyan, A.Kh. Ayvazyan, V.S. Mirzoyan, G.M. Paronikyan, T.P. Sarkisyan, G.M. Stepanyan, F.G. Arsenyan, B.T. Garibdzhanyan, Pharm. Chem. J. 21, 403 (1987) http://dx.doi.org/10.1007/BF0075862710.1007/BF00758627Search in Google Scholar

[9] A.G.M. Barrett, G.G. Graboski, Chem. Rev. 86, 751 (1985) http://dx.doi.org/10.1021/cr00075a00210.1021/cr00075a002Search in Google Scholar

[10] N. Ono, The nitro group in organic synthesis, (Wiley-VCH, Weinheim, 2001) http://dx.doi.org/10.1002/047122448010.1002/0471224480Search in Google Scholar

[11] R. Ballini, M. Petrini, Tetrahedron 60, 1017 (2004) http://dx.doi.org/10.1016/j.tet.2003.11.01610.1016/j.tet.2003.11.016Search in Google Scholar

[12] G.W. Kabalka, L.H.M. Guindi, R.S. Varma, Tetrahedron 46, 7443 (1990) http://dx.doi.org/10.1016/S0040-4020(01)89059-110.1016/S0040-4020(01)89059-1Search in Google Scholar

[13] Z. Rappaport, J.F. Liebman, In: Z. Rappaport (Ed.), The Chemistry of functional groups (Wiley, Chichester, 2009) vol. 1 Search in Google Scholar

[14] L.I. Belenkii, In: H. Feuer (Ed.), Nitrile oxides, nitrone and nitronates in orgnanic synthesis (Wiley, Chichester, New York, 2007) Search in Google Scholar

[15] V.Yu. Korotayev, A.Yu. Barkov, P.A. Slepukhin, M.I. Kodess, V.Ya. Sosnovskikh, Mendeleev Commun. 21, 112 (2011) http://dx.doi.org/10.1016/j.mencom.2011.03.02010.1016/j.mencom.2011.03.020Search in Google Scholar

[16] V.Yu. Korotayev, V.Ya. Sosnovskikh, M.A. Barabanov, A.Yu. Barkov, M.I. Kodess, Mendeleev. Commun. 17, (2010) Search in Google Scholar

[17] J.P. Agrawal, R.D. Hodgson, Chemistry of explosives (Wiley, Chichester, Hoboken, 2007) 10.1002/9780470059364Search in Google Scholar

[18] C.C. Novikov, G.A. Shvekhgeimer, V.V. Sevastyanova, V.A. Shlaposhnikov, Khimiya alifaticheskikh i alitsiklicheskikh nitrosoedinenii (Izd. Khimya, Moscow, 1974) (in Russian) Search in Google Scholar

[19] R. Jasiński, A. Barański, Polish J. Chem. 80, 1493 (2006) Search in Google Scholar

[20] R. Jasiński, M. Mikulska, A. Barański, Acta Chim. Slov. 58, 41 (2011) Search in Google Scholar

[21] R. Jasiński, M. Mikulska, A. Barański, Central Eur. J. Chem. 11, 1471 (2013) http://dx.doi.org/10.2478/s11532-013-0276-610.2478/s11532-013-0276-6Search in Google Scholar

[22] R. Jasiński, A. Lyubimcev, A. Ciężkowska, A. Barański, Chem. Heterocyclic Compd. 40, 206 (2004) Search in Google Scholar

[23] R. Jasiński, O. Koifman, A. Barański, Mendeleev Commun. 21, 262 (2011) http://dx.doi.org/10.1016/j.mencom.2011.09.01010.1016/j.mencom.2011.09.010Search in Google Scholar

[24] R. Jasiński, Tetrahedron 69, 927 (2013) http://dx.doi.org/10.1016/j.tet.2012.10.09510.1016/j.tet.2012.10.095Search in Google Scholar

[25] P. Perez, L.R. Domingo, M.J. Aurell, R. Contreras, Tetrahedron 59, 3117 (2003) http://dx.doi.org/10.1016/S0040-4020(03)00374-010.1016/S0040-4020(03)00374-0Search in Google Scholar

[26] P. Perez, L.R. Domingo, A. Aizman, R. Contreras, In: A. Toro-Labbé (Ed.), Theoretical and Computational Chemistry (Elsevier, Amsterdam, Boston, 2007) vol. 1 Search in Google Scholar

[27] Barański, R. Jasiński, Wiad. Chem. 56, 829 (2002) (in Polish) Search in Google Scholar

[28] A. Barański, V.I. Kelarev, Chem. Heterocyclic Compd. 26, 371 (1990) http://dx.doi.org/10.1007/BF0049720410.1007/BF00497204Search in Google Scholar

[29] R. Huisgen, In: A. Padwa (Ed.), 1,3-Dipolar Cycloaddition Chemistry (Wiley Interscience, New York, 1984) Search in Google Scholar

[30] G. Wagner, T. Garlan, Tetrahedron Lett. 49, 3596 (2008) http://dx.doi.org/10.1016/j.tetlet.2008.04.01210.1016/j.tetlet.2008.04.012Search in Google Scholar

[31] G.D. Buckley, C.W. Scaife, J. Chem. Soc. 1417 (1947) Search in Google Scholar

[32] E. Schmidt, G. Rutz, Ber. Dtsch. Chem. Ges. 61, 2142 (1928) http://dx.doi.org/10.1002/cber.1928061091510.1002/cber.19280610915Search in Google Scholar

[33] F. Brower, H. Burkett, J. Am. Chem. Soc. 75, 1082 (1953) http://dx.doi.org/10.1021/ja01101a02110.1021/ja01101a021Search in Google Scholar

[34] M.J. Frisch, G.W. Trucks, H.B. Schlegel, G.E. Scuseria, M.A. Robb, J.R. Cheeseman, J.A. Montgomery, T. Jr. Vreven, K.N. Kudin, J.C. Burant, J.M. Millam, S.S. Iyengar, J. Tomasi, V. Barone, B. Mennucci, M. Cossi, G. Scalmani, N. Rega, G.A. Petersson, H. Nakatsuji, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, Y. Nakajima, O. Honda, O. Kitao, H. Nakai, M. Klene, X Li, J.E. Knox, H.P. Hratchian, J.B. Cross, C. Adamo, J. Jaramillo, R. Gomperts, R.E. Stratmann, O. Yazyev, A.J. Austin, R. Cammi, C. Pomelli, J.W. Ochterski, P.Y. Ayala, K. Morokuma, G.A. Voth, P. Salvador, J.J. Dannenberg, V.G. Zakrzewski, S. Dapprich, A.D. Daniels, M.C. Strain, M.C. Farkas, D.K. Malick, A.D. Rabuck, K. Raghavachari, J.B. Foresman, J.V. Ortiz, Q. Cui, A.G. Baboul, S. Clifford, J. Cioslowski, B.B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R.L. Martin, D. J. Fox, T. Keith, M.A. Al-Laham, C.Y. Peng, A. Nanayakkara, M. Challacombe, P.M.W. Gill, B. Johnson, W. Chen, M.W. Wong, C. Gonzalez,. J.A. Pople, Gaussian 03, Revision B.04 (Gaussian, Inc., Pittsburgh PA, 2003) Search in Google Scholar

[35] J. Tomasi, B. Mennucci, E. Cancès, J. Mol. Struct. (Theochem) 464, 211 (1999) http://dx.doi.org/10.1016/S0166-1280(98)00553-310.1016/S0166-1280(98)00553-3Search in Google Scholar

[36] E. Pretsch, P. Bullmann, C. Affolter, Structure Determination of Organic Compounds; Tables of Spectral Data (Springer-Verlag, Berlin, Heidelberg, 2000) http://dx.doi.org/10.1007/978-3-662-04201-410.1007/978-3-662-04201-4Search in Google Scholar

[37] P. Grunager, P. Vita-Finzi, In: A. Padwa (Ed.), The Chemistry of Heterocyclic Compounds (Wiley & Sons, New York, 1991) vol.49 Search in Google Scholar

[38] P.K. Chattaraj, S. Giri, S. Duley, Chem. Rev. 111, PR43 (2011) 10.1021/cr100149pSearch in Google Scholar

[39] L.R. Domingo, E. Chamorro, P. Perez, J. Org. Chem. 73, 4615 (2008) http://dx.doi.org/10.1021/jo800572a10.1021/jo800572aSearch in Google Scholar

[40] P. Perez, L.R. Domingo, M. Duque-Norena, E. Chamorro, J. Mol. Struct. (TheoChem), 895, 86 (2009) http://dx.doi.org/10.1016/j.theochem.2008.10.01410.1016/j.theochem.2008.10.014Search in Google Scholar

[41] D. Ginsburg, Tetrahedron 39, 2095 (1983) http://dx.doi.org/10.1016/S0040-4020(01)91928-310.1016/S0040-4020(01)91928-3Search in Google Scholar

[42] L.R. Domingo, J.A. Saez, Org. Biomol. Chem. 7, 3576 (2009) http://dx.doi.org/10.1039/b909611f10.1039/b909611fSearch in Google Scholar PubMed

[43] K. Tanaka, T. Mori, K. Mitsuhashi, Bull. Chem. Soc. Japan 66, 263 (1993) http://dx.doi.org/10.1246/bcsj.66.26310.1246/bcsj.66.263Search in Google Scholar

Published Online: 2014-2-21
Published in Print: 2014-5-1

© 2014 Versita Warsaw

This work is licensed under the Creative Commons Attribution-NonCommercial-NoDerivatives 3.0 License.

Scroll Up Arrow