Abstract
The 1,3-dipolar cycloaddition products of C,N-disubstituted nitrones and different in situ prepared mono-N-substituted nitrones to η6-(styrene) chromium tricarbonyl and η6-(ethyl cynnamate) chromium tricarbonyl were synthesized and characterized by HPLC, IR, 1H NMR spectroscopy, and mass spectrometry. The resulted isoxazolidines were produced with a full regioselectivity and high stereoselectivity reached 100% in most cases.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
References
R. Huisgen, Angew. Chem., Int. Ed., 1968, 7, 321.
R. Huisgen, J. Org. Chem., 1968, 33, 2291.
R. Huisgen, Helv. Chim. Acta, 1967, 50, 2421.
J. J. Tufariello, Acc. Chem. Res., 1979, 12, 396.
J. J. Tufariello, in 1,3-Dipolar Cycloaddition Chemistry, Ed. A. Padwa, John Wiley and Sons, New York, 1984, Vol. 2, p. 83.
P. N. Confalone, E. M. Huie, Org. React., 1988, 36, 1.
G. A. Schiehser, J. D. White, G. Matsumoto, J. O. Pezzanite, J. Clardy, Tetrahedron Lett., 1986, 27, 5587.
A. E. McCaig, R. H. Wightman, Tetrahedron Lett., 1993, 34, 3939.
A. Goti, F. Cardona, A. Brandi, S. Picasso, P. Vogel, Tetrahedron: Asymmetry, 1996, 7, 1659.
D. Kiers, D. Moffat, K. Overton, J. Chem. Soc., Chem. Commun., 1988, 654.
D. Kiers, D. Moffat, K. Overton, R. J. Tomanek, Chem. Soc., Perkin Trans. 1, 1991, 1041.
C. M. Tice, B. Ganem, J. Org. Chem., 1983, 48, 5048.
A. Vasella, R. Voeffray, J. Chem. Soc., Chem. Commun., 1981, 97.
A. Vasella, R. Voeffray, Helv. Chim. Acta, 1982, 65, 1134.
C. Mukai, I. J. Kim, W. J. Cho, M. Hanaoka, Tetrahedron Lett., 1990, 31, 6893.
M. Rosillo, G. Dominguez, J. Perez-Castells, Chem. Soc. Rev., 2007, 36, 1589.
F. Rose-Munch, E. Rose, in Modern Arene Chemistry, Ed. D. Astruc, Willy-VCH, 2003, p. 368.
S. E. Gibson, H. Ibrahim, Chem. Commun., 2002, 21, 2465.
E. J. Fornefeld, A. J. Pike, J. Org. Chem., 1979, 44, 835.
K. Heusler, P. Wieland, Ch. Meystre, Org. Synth., 1973, 5, 1124.
C. Mukai, I. J Kim, W. J. Cho, M. Kido, M. Hanaoka, J. Chem. Soc., Perkin Trans. 1, 1993, 2495.
W. D. Emmons, J. Am. Chem. Soc., 1957, 79, 5739.
M. D. Raush, G. A. Moser, E. S. Zaiko, A. L. Lipman, J. Organomet. Chem., 1970, 23, 185.
N. B. Valetova, A. N. Artemov, D. F. Grishin, Izv. Vyssh. Uchebn. Zaved., Khimiya and Khim. Tekhnologiya, 2007, 50, No. 9, 80 (in Russian).
K.N. Houk, J. Am. Chem. Soc., 1972, 94, 8953.
K. N. Houk, A. Bimanand, D. Mukherjee, J. Sims, Y.-M. Chang, D. C. Kaufman, N. L. Domelsmith, Heterocycles, 1977, 7, 293.
J. P. Freeman, Chem. Rev., 1983, 63, 241.
I. V. Bodrikov, I. I. Grinval’d, A. N. Artemov, L. I. Bazhan, I. Yu. Kalagaev, Zh. Obshch. Khim., 2010, 80, 24 [Russ. J. Gen. Chem. (Engl. Transl.), 2010, 80, 20].
R. Huisgen, R. Grashey, H. Hawk, H. Seidl, Chem. Ber., 1968, 101, 2548.
W. J. Bland, R. Davis, J. L. A. Durrant, J. Organomet. Chem., 1982, 234, C20.
C. Weygand, Organisch-Chemische Experimentierkunst, 2. Auflage, Johann Ambrosius Barth, Leipzig, 1948, 824 S.
V. V. Shpanova, V. S. Volodina, Preparativnaya organicheskaya khimiya [Preparative Organic Chemistry], Ed. N. S. Wulfson, Goskhimizdat, Moscow, 1959, p. 594 [Preparatyka organiczna, Panstwowe wydawnictwa techniczne, Warszawa, 1954, 1187 s.]
G. M. Sheldrick, SADABS, 1997, Bruker AXS, Inc., Madison (WI), USA.
G. M. Sheldrick, Acta Crystallogr., Sect. A: Found. Crystallogr., 2008, 64, 112.
Author information
Authors and Affiliations
Corresponding author
Additional information
Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 11, pp. 2059–2064, November, 2012.
Rights and permissions
About this article
Cite this article
Artemov, A.N., Sazonova, E.V., Mavrina, E.A. et al. Synthesis of new η6-(arene) chromium tricarbonyl complexes of isoxazolidines by 1,3-dipolar cycloaddition. Russ Chem Bull 61, 2076–2081 (2012). https://doi.org/10.1007/s11172-012-0290-4
Received:
Revised:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s11172-012-0290-4