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Issue 10, 2013
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Tandem ionic liquid antimicrobial toxicity and asymmetric catalysis study: carbonyl-ene reactions with trifluoropyruvate

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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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Supplementary files

Article information


Submitted
11 May 2013
Accepted
09 Jul 2013
First published
13 Aug 2013

Green Chem., 2013,15, 2727-2739
Article type
Paper

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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