Issue 10, 2013
From the journal:

Green Chemistry

Tandem ionic liquid antimicrobial toxicity and asymmetric catalysis study: carbonyl-ene reactions with trifluoropyruvate†

Rohitkumar G. Gore,a   Thi-Kim-Thu Truong,a   Milan Pour,b   Lauren Myles,c   Stephen J. Connon*c  and  Nicholas Gathergood*a  

* Corresponding authors

a School of Chemical Sciences and National Institute for Cellular Biotechnology, Dublin City University, Glasnevin, Dublin 9, Ireland
E-mail: Nick.Gathergood@dcu.ie
Fax: +35 317005503

b Centre for New Antivirals and Antineoplastics, Department of Inorganic and Organic Chemistry, Charles University, Faculty of Pharmacy, Heyrovskeho 1203, CZ-500 03, Hradec Kralove, Czech Republic

c Trinity Biomedical Sciences Institute, School of Chemistry, University of Dublin, Trinity College, Dublin 2, Ireland
E-mail: connons@tcd.ie
Fax: +35 316712826

Abstract

The asymmetric carbonyl-ene reaction of trifluoropyruvate with five alkenes catalysed by [Pd{(R)-BINAP}](SbF6)2 were carried out in good yields and enantioselectivities (up to 96% yield and 96% ee) in low antimicrobial toxicity C2-substituted imidazolium ionic liquids (ILs). Toxicity data was included in the selection criteria for reaction optimisation after a preliminary IL screen. The Pd(II) catalyst immobilised in an IL was recycled and reused up to 7 times without decrease of either yield or ee. One IL prepared, which was determined to be of high antimicrobial toxicity was assigned a low priority for future applications.

Graphical abstract: Tandem ionic liquid antimicrobial toxicity and asymmetric catalysis study: carbonyl-ene reactions with trifluoropyruvate

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Article information

DOI
https://doi.org/10.1039/C3GC40875B
Article type
Paper
Submitted
11 May 2013
Accepted
09 Jul 2013
First published
13 Aug 2013

Green Chem., 2013,15, 2727-2739

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Tandem ionic liquid antimicrobial toxicity and asymmetric catalysis study: carbonyl-ene reactions with trifluoropyruvate

R. G. Gore, T. Truong, M. Pour, L. Myles, S. J. Connon and N. Gathergood, Green Chem., 2013, 15, 2727 DOI: 10.1039/C3GC40875B

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