Collect. Czech. Chem. Commun. 2002, 67, 1359-1365
https://doi.org/10.1135/cccc20021359

Synthesis of (Trifluoromethyl)aziridines in 1,1,1,3,3,3-Hexafluoropropan-2-ol: First Example of Coupling Reactions of Fluoral, an Amine and a Diazo Compound

Maria Vittoria Spanedda, Benoit Crousse*, Satoru Narizuka, Danièle Bonnet-Delpon* and Jean-Pierre Bégué

BioCIS, Centre d'Etudes Pharmaceutiques, rue J. B. Clément, Châtenay-Malabry, F-92296 Cedex, France

References

1a. Muller P. in: Advances in Catalytic Processes (M. P. Doyle, Ed.), Vol. 2. JAI Press, Greenwich (CT) 1997.
1b. Pearson W. H., Lian B. W., Bergmeier S. C. in: Comprehensive Heterocyclic Chemistry II (Padwa, A. Ed.), Vol. 1A, p. 1. Pergamon Press, Oxford 1996.
1c. Kump J. E. G. in: Comprehensive Organic Synthesis (B. M. Trost and I. Fleming, Eds), Vol. 7, p. 469. Pergamon, Oxford 1991.
1d. Tanner D.: Angew. Chem., Int. Ed. Engl. 1994, 33, 599. <https://doi.org/10.1002/anie.199405991>
1e. Tanner D.: Pure Appl. Chem. 1993, 65, 1319. <https://doi.org/10.1351/pac199365061319>
1f. Hudlicky T., Seoane G., Price J. D., Gadamasetti K. G.: Synlett 1990, 433. <https://doi.org/10.1055/s-1990-21120>
2a. Rasmussen K. G., Jorgensen K. A.: J. Chem. Soc., Chem. Commun. 1995, 1401. <https://doi.org/10.1039/c39950001401>
2b. Hansen K. B., Einnez N. S., Jacobsen E. N.: Angew. Chem., Int. Ed. Engl. 1995, 34, 676. <https://doi.org/10.1002/anie.199506761>
2c. Zhu Z., Espenson J. H.: J. Org. Chem. 1995, 60, 7090. <https://doi.org/10.1021/jo00127a008>
2d. Zhu Z., Espenson J. H.: J. Am. Chem. Soc. 1996, 118, 9901. <https://doi.org/10.1021/ja954039t>
2e. Mohan J. M., Uphade B. S., Choudhary V. R., Ravingranathan T., Sudalai A.: J. Chem. Soc., Chem. Commun. 1997, 1429. <https://doi.org/10.1039/a702745a>
3a. Xie W., Fang J., Li J., Wang P. G.: Tetrahedron 1999, 55, 12929. <https://doi.org/10.1016/S0040-4020(99)00791-7>
3b. Nagayama S., Kobayashi S.: Chem. Lett. 1998, 685. <https://doi.org/10.1246/cl.1998.685>
3c. Rasmussen K. G., Jorgensen K. A.: J. Chem. Soc., Perkin Trans. 1 1997, 1287. <https://doi.org/10.1039/a608098g>
3d. Casarrubios L., Peraz J. A., Brookhart M., Templeton J. L.: J. Org. Chem. 1996, 61, 8358. <https://doi.org/10.1021/jo961391w>
3e. Mayer M. F., Hossain M. M.: J. Org. Chem. 1998, 63, 6839. <https://doi.org/10.1021/jo9804792>
3f. Juhl K., Hazell R. G., Jorgensen K. A.: J. Chem. Soc., Perkin Trans. 1 1999, 2293. <https://doi.org/10.1039/a903521d>
3g. Sengupta S., Mondal S.: Tetrahedron Lett. 2000, 41, 6245. <https://doi.org/10.1016/S0040-4039(00)01042-X>
4a. Crousse B., Narizuka S., Bonnet-Delpon D., Bégué J. P.: Synlett 2001, 679. <https://doi.org/10.1055/s-2001-13364>
4b. Only one example of the preparation of trans-(trifluoromethyl)aziridines was described involving the ring closure of 2-bromo(trifluoromethyl)amines: Davoli P., Forni A., Franciosi C., Moretti I., Prati F.: Tetrahedron: Asymmetry 1999, 10, 2361.
5. Xie W., Fang J., Li J., Wang P. G.: Tetrahedron 1999, 55, 12929. <https://doi.org/10.1016/S0040-4020(99)00791-7>
6a. Kamlet M. J., Abboud J.-L. M., Abraham M. H., Taft R. W.: J. Org. Chem. 1983, 48, 2877. <https://doi.org/10.1021/jo00165a018>
6b. Eberson L., Hartshorn M. P., Persson O., Radner F.: J. Chem. Soc., Chem. Commun. 1996, 2105. <https://doi.org/10.1039/cc9960002105>
7. Nagayama S., Kobayashi S.: Chem. Lett. 1998, 685. <https://doi.org/10.1246/cl.1998.685>