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

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Títol: Assessment of the organocatalytic activity of chiral l-Proline-based Deep Eutectic Solvents based on their structural features
Autors: Tiecco, Matteo | Alonso, Diego A. | Ros Ñíguez, Diego | Ciancaleoni, Gianluca | Guillena, Gabriela | Ramón, Diego J. | Apio Bonillo, Alberto | Germani, Raimondo
Grups d'investigació o GITE: Catálisis Estereoselectiva en Síntesis Orgánica (CESO) | Alternative Methodologies In Chemistry (AMIC)
Centre, Departament o Servei: Universidad de Alicante. Departamento de Química Orgánica | Universidad de Alicante. Instituto Universitario de Síntesis Orgánica
Paraules clau: Deep Eutectic Solvents | Enantioselectivity | Green chemistry | Asymmetric organocatalysis | Active solvents
Àrees de coneixement: Química Orgánica
Data de publicació: 1-de setembre-2020
Editor: Elsevier
Citació bibliogràfica: Journal of Molecular Liquids. 2020, 313: 113573. doi:10.1016/j.molliq.2020.113573
Resum: 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.
Patrocinadors: 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).
ISSN: 0167-7322 (Print) | 1873-3166 (Online)
DOI: 10.1016/j.molliq.2020.113573
Idioma: eng
Tipus: info:eu-repo/semantics/article
Drets: © 2020 Elsevier B.V.
Revisió científica: si
Versió de l'editor:
Apareix a la col·lecció: INV - CESO - Artículos de Revistas
INV - AMIC - Artículos de Revistas

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