Abstract
The synthesis of 1-(S)-α-phenylethyl-3,3-dimethyldiaziridine from N-(S)-α-phenylacetonimine and hydroxylamine-O-sulfonic acid has been carried out with high diastereoselectivity. The absolute configuration of the diastereomers was established by comparison with oxaaziridine analogs based on their NMR and CD spectra, and atom-atomic potential calculations. A test has been proposed to establish the absolute configuration of N-α-phenylethyl-substituted three-membered ring heterocycles using NMR, and the mechanism of epimination of imines is discussed, which is similar to their oxidation mechanism.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
Literature Cited
I. I. Chervin, A. A. Fomichev, N. L. Zaichenko, A. E. Aliev, A. S. Moskalenko, A. V. Prosyanik, V. N. Vosnesenskii, and R. G. Kostyanovskii, Izv. Akad. Nauk SSSR, Ser. Khim., No. 5, 1110 (1988).
C. J. Paget and C. S. Davis, J. Med. Chem.,7, 626 (1964).
R. G. Kostyanovskii, G. V. Shustov, O. G. Nabiev, S. N. Denisenko, S. A. Sukhanova, and E. F. Lavretskaya, Khim.-farm. Zh., No. 6, 671 (1986).
R. G. Kostyanovskii, G. V. Shustov, A. I. Mishchenko, and V. I. Markov, Izv. Akad. Nauk SSSR, Ser. Khim., No. 9, 2026 (1976).
R. G. Kostyanovsky, G. V. Shustov, and. N. L. Zaichenko, Tetrahedron,98, 949 (1982).
G. V. Shustov, S. N. Denisenko, and R. G. Kostyanovskii, Izv. Akad. Nauk SSSR, Ser. Khim., No. 8, 1831 (1986).
H. Dorn and K. Walter, Annalen,720, 98 (1969).
C. Belzecki and D. Mostowicz, J. Org. Chem.,40, 3878 (1975).
M. Bucciarelli, A. Forni, I. Moretti, and G. Torre, J. Chem. Soc. Perkin Trans. 2, No. 10, 1339 (1977).
A. V. Eremeev, F. D. Polyak, A. F. Mishnev, and Ya. Ya. Bleidelis, Izv. Akad. Nauk SSSR, Ser. Khim., No. 2, 229 (1985).
G. V. Shustov, A. B. Zolotoi, N. L. Zaichenko, O. A. Dyachenko, L. O. Atovmyan, and R. G. Kostyanovsky, Tetrahedron,40, 2151 (1984).
M. Bogucka-Ledochowska, A. Konitz, A. Hempel, Z. Dauter, E. Borowski, C. Belzecki, and D. Mostowicz, Tetrahedron Lett., No. 13, 1025 (1976).
A. Forni, G. Garutti, I. Moretti, G. Torre, G. D. Andreetti, G. Bocelli, and P. Sgarabotto, J. Chem. Soc., Perkin 2, No. 5, 401 (1978).
A. Lattes, E. Oliveros, M. Riviere, C. Belzecki, D. Mostowicz, W. Abramskj, C. Pic-cinni-Leopardi, G. Germain, and M. Van Meersshe, J. Am. Chem. Soc.,104, 3929 (1982).
D. R. Boyd, K. M. McCombe, T. A. Hamor, W. B. Jennings, and V. E. Wilson, J. Chem. Soc., Perkin 2, No. 1, 95 (1984).
E. Schmitz, Three-Membered Rings Containing Two Heteroatoms [Russian translation], Mir, Moscow (1970).
V. I. Sokolov, Introduction to Theoretical Stereochemistry [in Russian], Nauka, Moscow (1979).
F. A. Momany, L. C. Carruthers, R. F. McGuire, and H. A. Sheraga, J. Phys. Chem.,78, 1595 (1974).
V. G. Dashevskii, Conformations of Organic Molecules [in Russian], Khimiya, Moscow (1974).
Author information
Authors and Affiliations
Additional information
Communication 60 in the series “Asymmetric Nitrogen”; for Communication 59, see [1].
Translated from Geterotsiklicheskikh Soedinenii, No. 11, pp. 1461–1465, November, 1988.
Rights and permissions
About this article
Cite this article
Shustov, G.V., Polyak, F.D., Nosova, V.S. et al. Diastereoselective synthesis of 1-α-phenylethyl-3,3-dimethyldiaziridine. Conformation and configuration of three-membered ring nitrogen heterocycles containing an asymmetric substituent on the nitrogen atom. Chem Heterocycl Compd 24, 1207–1211 (1988). https://doi.org/10.1007/BF00633496
Received:
Issue Date:
DOI: https://doi.org/10.1007/BF00633496