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

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Título: Assessment of the organocatalytic activity of chiral l-Proline-based Deep Eutectic Solvents based on their structural features
Autor/es: Tiecco, Matteo | Alonso, Diego A. | Ros Ñíguez, Diego | Ciancaleoni, Gianluca | Guillena, Gabriela | Ramón, Diego J. | Apio Bonillo, Alberto | Germani, Raimondo
Grupo/s de investigación o GITE: Catálisis Estereoselectiva en Síntesis Orgánica (CESO) | Alternative Methodologies In Chemistry (AMIC)
Centro, Departamento o Servicio: Universidad de Alicante. Departamento de Química Orgánica | Universidad de Alicante. Instituto Universitario de Síntesis Orgánica
Palabras clave: Deep Eutectic Solvents | Enantioselectivity | Green chemistry | Asymmetric organocatalysis | Active solvents
Área/s de conocimiento: Química Orgánica
Fecha de publicación: 1-sep-2020
Editor: Elsevier
Cita bibliográfica: Journal of Molecular Liquids. 2020, 313: 113573. doi:10.1016/j.molliq.2020.113573
Resumen: 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.
Patrocinador/es: 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
Idioma: eng
Tipo: info:eu-repo/semantics/article
Derechos: © 2020 Elsevier B.V.
Revisión científica: si
Versión del editor: https://doi.org/10.1016/j.molliq.2020.113573
Aparece en las colecciones:INV - CESO - Artículos de Revistas
INV - AMIC - Artículos de Revistas

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