Copper Oxide Nanoparticles-Catalyzed Aziridine Ring Opening with Diaryl Diselenides Under Ionic Liquid as Reaction Medium

Copper Oxide Nanoparticles-Catalyzed Aziridine Ring Opening with Diaryl Diselenides Under Ionic Liquid as Reaction Medium

Braga, Antonio Luiz; Salman, Syed M.; Muhamamd, Sayyar; Rodrigues, Oscar E. D.; Dornelles, Luciano; Schwab, Ricardo S.

Abstract:

The development of new methods for the introduction of selenium-containing groups into organic molecules remains a significant challenge. Moreover, chiral selenide- and diselenides containing ligands offer attractive and practical options in the development of asymmetric transformations. In this context, a straightforward synthesis of a new set of chiral _-seleno amine through a stereoselective aziridine ring opening with selenium nucleophiles, generated by reducing agents such as NaBH4, LiBHEt3, zinc or indium salts have been described by our group. We herein report an ecofriendly procedure for the synthesis of chiral _-seleno amine under mild conditions, using selenium nucleophile generated by base in the presence of CuO nanopowder as a catalyst in ionic liquid BMIM[BF4] as solvent.

The development of new methods for the introduction of selenium-containing groups into organic molecules remains a significant challenge. Moreover, chiral selenide- and diselenides containing ligands offer attractive and practical options in the development of asymmetric transformations. In this context, a straightforward synthesis of a new set of chiral _-seleno amine through a stereoselective aziridine ring opening with selenium nucleophiles, generated by reducing agents such as NaBH4, LiBHEt3, zinc or indium salts have been described by our group. We herein report an ecofriendly procedure for the synthesis of chiral _-seleno amine under mild conditions, using selenium nucleophile generated by base in the presence of CuO nanopowder as a catalyst in ionic liquid BMIM[BF4] as solvent.

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DOI: 10.5151/chempro-14bmos-R0026-1

Referências bibliográficas

• [1] 1. Braga, A. L.; Lüdtke, D. S.; Vargas, F.; Braga, R. C. Synlett 2006, 1453.
• [2] 2. (a) Braga, A. L.; Lüdtke, D. S.; Paixão, M. W.; Rodrigues, O. E. D. Org. Lett. 2003, 5, 2635; (b) Braga, A. L.; Paixão, M. W.; Marin, G. Synlett 2005, 1675; (c) Braga, A. L.; Schneider, P. H.; Paixão, M. W.; Deobald, A. M.; Peppe, C.; Bottega, D. P. J. Org. Chem. 2006, 71, 4305. (d) Braga, A. L.; Schwab, R. S.; Alberto, E. E.; Salman, S. M. Vargas, J.; Azeredo, J. B. Tetrahedron Lett. 2009, 50, 2309.

Como citar:

Braga, Antonio Luiz; Salman, Syed M.; Muhamamd, Sayyar; Rodrigues, Oscar E. D.; Dornelles, Luciano; Schwab, Ricardo S.; "Copper Oxide Nanoparticles-Catalyzed Aziridine Ring Opening with Diaryl Diselenides Under Ionic Liquid as Reaction Medium", p-26-26. In: In Blucher Chemistry Proceedings, São Paulo, v. 1, n. 1, Setembro.2013. São Paulo: Blucher, 2013.
ISSN 23184043, DOI 10.5151/chempro-14bmos-R0026-1