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Synlett 2011(1): 69-72  
DOI: 10.1055/s-0030-1259082
LETTER
© Georg Thieme Verlag Stuttgart ˙ New York

Efficient Ring Opening of Protected and Unprotected Aziridines Promoted by Stable Zinc Selenolate in Ionic Liquid

Syed M. Salmana, Ricardo S. Schwaba, Eduardo E. Albertoa, Josimar Vargasa, Luciano Dornelles*a, Oscar E. D. Rodrigues*a, Antonio L. Braga*b
a Departamento de Química, Universidade Federal de Santa Maria, 97105-900 Santa Maria, RS, Brazil
e-Mail: rodriguesoed@ymail.com;
b Departamento de Química, Universidade Federal de Santa Catarina, 88040-970 Florianópolis, SC, Brazil
e-Mail: albraga@qmc.ufsc.br;
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Publication History

Received 1 October 2010
Publication Date:
07 December 2010 (online)

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Abstract

A highly efficient protocol is reported for the synthesis of chiral β-seleno amines via the ring-opening reaction of aziridines. Under neutral conditions, employing a stable phenyl selenolate specie (PhSeZnBr) and (BMIM)BF4 as solvent, β-seleno amines were obtained in good to excellent yields. Reuse of the ionic liquid was also possible, and four runs were performed with no decrease in the yields.

Key words

chiral β-seleno amines - ring opening reaction - aziridine - ionic liquid

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Detailed procedure in the Supporting Information.