Issue 32, 2012
From the journal:

Organic & Biomolecular Chemistry

Ephedrine-based diselenide: a promiscuous catalyst suitable to mimic the enzyme glutathione peroxidase (GPx) and to promote enantioselective C–C coupling reactions†

Letiére C. Soares,a   Eduardo E. Alberto,b   Ricardo S. Schwab,c   Paulo S. Taube,d   Vanessa Nascimento,d   Oscar E. D. Rodriguesa  and  Antonio L. Braga*d  

* Corresponding authors

a NanoBio, Dpto de Química, CCNE, Universidade Federal de Santa Maria, Santa Maria, RS, Brazil

b Chemistry Department, The State University of New York at Buffalo, Buffalo, NY, USA

c Instituto de Química, Universidade Federal do Rio Grande do Sul, Porto Alegre, RS, Brazil

d Laboratório de Síntese de Substâncias de Selênio Bioativas CFM, Departamento de Química, Universidade Federal de Santa Catarina, Florianópolis, SC, Brazil
E-mail: albraga@qmc.ufsc.br
Tel: +55 (48) 37216427

Abstract

The ephedrine-based diselenide appears as a new promiscuous catalyst, able to generate optically active alcohols by addition of organozinc to aldehydes (up to 97% ee), and shows powerful GPx like activity, reducing H2O2 to water in only 16.33 min (eleven times faster than PhSeSePh).

Graphical abstract: Ephedrine-based diselenide: a promiscuous catalyst suitable to mimic the enzyme glutathione peroxidase (GPx) and to promote enantioselective C–C coupling reactions

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Article information

DOI
https://doi.org/10.1039/C2OB25539A
Article type
Paper
Submitted
12 Mar 2012
Accepted
27 Jun 2012
First published
28 Jun 2012

Org. Biomol. Chem., 2012,10, 6595-6599

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Ephedrine-based diselenide: a promiscuous catalyst suitable to mimic the enzyme glutathione peroxidase (GPx) and to promote enantioselective C–C coupling reactions

L. C. Soares, E. E. Alberto, R. S. Schwab, P. S. Taube, V. Nascimento, O. E. D. Rodrigues and A. L. Braga, Org. Biomol. Chem., 2012, 10, 6595 DOI: 10.1039/C2OB25539A

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