Synthesis and structural characterization of l-prolinol derived chiral eutectic mixtures as sustainable solvents in asymmetric organocatalysis

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Title: Synthesis and structural characterization of l-prolinol derived chiral eutectic mixtures as sustainable solvents in asymmetric organocatalysis
Authors: Ñíguez, José A. | Burlingham, Sarah-Jayne | Chinchilla, Rafael | Pérez, Juana M. | Fernández, Ignacio | Alonso, Diego A.
Research Group/s: Catálisis Estereoselectiva en Síntesis Orgánica (CESO)
Center, Department or Service: Universidad de Alicante. Departamento de Química Orgánica | Universidad de Alicante. Instituto Universitario de Síntesis Orgánica
Keywords: L-Prolinol-based chiral solvents | Organocatalytic properties | Synthesis | Characterization
Issue Date: 21-Dec-2023
Publisher: Royal Society of Chemistry
Citation: RSC Sustainability. 2024, 2: 499-509. https://doi.org/10.1039/D3SU00349C
Abstract: The present study focuses on the synthesis, characterization, and examination of the organocatalytic properties of a series of structurally novel L-Prolinol-based chiral solvents. Different L-Prolinol/TBAB and L-Prolinol/Glycolic acid (GA) mixtures have been characterized and evaluated for their structural characteristics using ATR-FTIR spectroscopy, differential scanning calorimetry (DSC), and NMR techniques including diffusion and NOESY NMR measurements. The structural characteristics of the L-Prolinol-based chiral solvents enabled these novel materials to display organocatalytic activities in the asymmetric conjugate addition of ketones to nitroolefins, showing the chiral liquid L-Prolinol/GA: 1/1 the highest yields and selectivities being similar or superior to those displayed by L-Prolinol in VOC or under neat conditions. Moreover, the new chiral liquid was successfully recovered and reused with minimal loss of performance over several cycles. Regarding the reaction mechanism, it has been detected a rapid formation of the oxazoline intermediate by NMR spectroscopy.
Sponsor: This research has been funded by Generalitat Valenciana (Project AICO 2021/013), Junta de Andalucía (projects 102C2000004, UAL2020-AGR-B1781 and P20_01041), the State Research Agency of the Spanish Ministry of Science, Innovation and Universities (projects PID2021-126445OB-I00, PDC2021-121248-I00, PID2020-119116RA-I00 and PID2021-127332NB-I00) together with EU FEDER funds, and the University of Alicante (Project VIGROB-173 and grants UAUSTI 2022). J. M. P. acknowledges the University of Almeria (grant no. HIPATIA2021_04) for her fellowship.
URI: http://hdl.handle.net/10045/139563
ISSN: 2753-8125
DOI: 10.1039/D3SU00349C
Language: eng
Type: info:eu-repo/semantics/article
Rights: This article is licensed under a Creative Commons Attribution-NonCommercial 3.0 Unported Licence.
Peer Review: si
Publisher version: https://doi.org/10.1039/D3SU00349C
Appears in Collections:INV - CESO - Artículos de Revistas

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