Next Article in Journal
Synthesis and Biochemical Evaluation of Warhead-Decorated Psoralens as (Immuno)Proteasome Inhibitors
Next Article in Special Issue
Toxicity of Zn-Fe Layered Double Hydroxide to Different Organisms in the Aquatic Environment
Previous Article in Journal
Solid-Phase Synthesis of Fluorescent Probes for Plasma Membrane Labelling
Previous Article in Special Issue
Recent Strategies and Applications for l-Asparaginase Confinement
Article

Room Temperature Ionic Liquids in Asymmetric Hetero-Ene Type Reactions: Improving Organocatalyst Performance at Lower Temperatures

1
Facultad de Ciencias Químicas, Instituto de Investigaciones en Físico-Química de Córdoba, Universidad Nacional de Córdoba, (INFIQC, CONICET-UNC), Haya de la Torre y Medina Allende, Ciudad Universitaria, Córdoba 5000, Argentina
2
Departamento de Química Orgánica, Universidad de Sevilla, c/Profesor García González 1, 41012 Sevilla, Spain
3
Instituto de Investigaciones Químicas (CSIC-US) and Centro de Innovación en Química Avanzada (ORFEO-CINQA), Avda. Américo Vespucio 49, 41092 Sevilla, Spain
*
Author to whom correspondence should be addressed.
Academic Editor: Giancarlo Cravotto
Molecules 2021, 26(2), 355; https://doi.org/10.3390/molecules26020355
Received: 14 December 2020 / Revised: 30 December 2020 / Accepted: 8 January 2021 / Published: 12 January 2021
Room temperature ionic liquids (RTILs) have been widely used as (co)solvents in several catalytic processes modifying, in most of the cases, the catalyst activity and/or the selectivity for the studied reactions. However, there are just a few examples of their use in hydrogen bonding organocatalysis. In this paper, we show the positive effect of a set of imidazole-based ionic liquids ([bmim]BF4 and [hmim]PF6) in the enantioselective addition of formaldehyde tert-butylhydrazone to prochiral α-keto esters catalyzed by a sugar-based chiral thiourea. Reactions performed in the presence of low percentages of RTILs led to an increase of the catalyst activity, thereby making possible to work at lower temperatures. Thus, the chiral tert-butyl azomethyl tertiary alcohols could be obtained with moderate to good conversions and higher enantioselectivities for most of the studied substrates when using up to 30 vol% of [hmim]PF6 as a cosolvent in processes performed in toluene. View Full-Text
Keywords: organocatalysis; ionic liquids; ene-type reactions; tertiary alcohols; solvent engineering; asymmetric catalysis organocatalysis; ionic liquids; ene-type reactions; tertiary alcohols; solvent engineering; asymmetric catalysis
Show Figures

Figure 1

MDPI and ACS Style

Bisogno, F.R.; Fernández, R.; Lassaletta, J.M.; de Gonzalo, G. Room Temperature Ionic Liquids in Asymmetric Hetero-Ene Type Reactions: Improving Organocatalyst Performance at Lower Temperatures. Molecules 2021, 26, 355. https://doi.org/10.3390/molecules26020355

AMA Style

Bisogno FR, Fernández R, Lassaletta JM, de Gonzalo G. Room Temperature Ionic Liquids in Asymmetric Hetero-Ene Type Reactions: Improving Organocatalyst Performance at Lower Temperatures. Molecules. 2021; 26(2):355. https://doi.org/10.3390/molecules26020355

Chicago/Turabian Style

Bisogno, Fabricio R., Rosario Fernández, Jose M. Lassaletta, and Gonzalo de Gonzalo. 2021. "Room Temperature Ionic Liquids in Asymmetric Hetero-Ene Type Reactions: Improving Organocatalyst Performance at Lower Temperatures" Molecules 26, no. 2: 355. https://doi.org/10.3390/molecules26020355

Find Other Styles
Note that from the first issue of 2016, MDPI journals use article numbers instead of page numbers. See further details here.

Article Access Map by Country/Region

1
Back to TopTop