Assessment of the organocatalytic activity of chiral l-Proline-based Deep Eutectic Solvents based on their structural features

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Title: Assessment of the organocatalytic activity of chiral l-Proline-based Deep Eutectic Solvents based on their structural features
Authors: Tiecco, Matteo | Alonso, Diego A. | Ros Ñíguez, Diego | Ciancaleoni, Gianluca | Guillena, Gabriela | Ramón, Diego J. | Apio Bonillo, Alberto | Germani, Raimondo
Research Group/s: Catálisis Estereoselectiva en Síntesis Orgánica (CESO) | Alternative Methodologies In Chemistry (AMIC)
Center, Department or Service: Universidad de Alicante. Departamento de Química Orgánica | Universidad de Alicante. Instituto Universitario de Síntesis Orgánica
Keywords: Deep Eutectic Solvents | Enantioselectivity | Green chemistry | Asymmetric organocatalysis | Active solvents
Knowledge Area: Química Orgánica
Issue Date: 1-Sep-2020
Publisher: Elsevier
Citation: Journal of Molecular Liquids. 2020, 313: 113573. doi:10.1016/j.molliq.2020.113573
Abstract: The impact on the environment of polluting and volatile organic solvents represents nowadays a severe problem. In order to reduce the incidence on the environment of chemical applications, Deep Eutectic Solvents (DESs) represent a step ahead in this field thanks to their green properties. These novel liquids are formed by inter- and intra-molecular weak interactions between two species and they are synthesized by simply heating and mixing them without any solvent. These solvents also show interesting catalytic capabilities, since their properties are truly tuneable. In this paper, l-Proline-based Chiral Deep Eutectic Solvents (CDESs) were prepared and used as green and organocatalytic reaction media in a probe asymmetric Michael addition; in this reaction the l-Proline acts as solvent component as well as chiral organocatalyst. The results were analysed with NMR studies taking in account the availability of the l-Proline, considering the strength of the association of it with the counterpart of the liquids. With DFT studies, the geometry and energy of the adducts are shown and a qualitative rationale to the reaction stereoisomers distribution is given.
Sponsor: This work was supported by the University of Pisa through the PRA_2018_36 grant, and by the Spanish Ministerio de Ciencia, Innovación y Universidades (MICINN, PGC2018-096616-B-I00) and the University of Alicante (VIGROB-173).
URI: http://hdl.handle.net/10045/107418
ISSN: 0167-7322 (Print) | 1873-3166 (Online)
DOI: 10.1016/j.molliq.2020.113573
Language: eng
Type: info:eu-repo/semantics/article
Rights: © 2020 Elsevier B.V.
Peer Review: si
Publisher version: https://doi.org/10.1016/j.molliq.2020.113573
Appears in Collections:INV - CESO - Artículos de Revistas
INV - AMIC - Artículos de Revistas

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