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Assessing the Recyclability of Supramolecularly Assembled Organocatalytic Species: A Theoretical Insight
Israel Journal of Chemistry ( IF 2.3 ) Pub Date : 2020-03-03 , DOI: 10.1002/ijch.201900178 Lluis Llorens 1, 2 , Patricia Llanes 1 , Mauro Fianchini 1 , Miquel A. Pericàs 1, 2
Israel Journal of Chemistry ( IF 2.3 ) Pub Date : 2020-03-03 , DOI: 10.1002/ijch.201900178 Lluis Llorens 1, 2 , Patricia Llanes 1 , Mauro Fianchini 1 , Miquel A. Pericàs 1, 2
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Asymmetric organocatalytic synthesis is a powerful tool in organic chemistry to achieve desired stereoisomers in high purity via mild catalytic routes. The immobilization of homogeneous catalytic species onto heterogeneous phases embodies the evolution of asymmetric catalysis, since it allows the recycling of the catalyst for several runs until degradation. Previously reported non‐covalent immobilization of proline‐based catalysts for aldol reaction onto magnetic nanoparticles functionalized with β‐cyclodextrin (MNP‐β‐CB) demonstrated the viability of the methodology. This paper proposes two new catalyst recycling strategies based on Cucurbit[7]uril (CB[7]) for the aldol reaction and the Robinson annulation. These recycling methodologies are conceptually different. The former relies on the homogeneous encapsulation of the catalyst in cucurbituril, CB[7] ⋅ Cat, and its recycling in the aqueous phase by extraction of the aldol product with organic solvents. The latter relies on the heterogeneous encapsulation of the catalyst as MNP‐CB[7] ⋅ Cat2 system and its recycling by magnetic harvesting. Density functional theory (DFT) calculations have been employed to rationalize the thermodynamics of experimental results, and to suggest caveats and plausible improvements in view of a future catalytic design.
中文翻译：
评估超分子组装的有机催化物种的可回收性：理论上的见解。
不对称有机催化合成是有机化学中强大的工具，可通过温和的催化途径以高纯度获得所需的立体异构体。将均相催化物种固定在非均相上体现了不对称催化的发展，因为它允许催化剂循环运行几次直至降解。先前报道的将脯氨酸基催化剂用于醛醇缩合反应的非共价固定在用β-环糊精（MNP-β-CB）功能化的磁性纳米颗粒上证明了该方法的可行性。本文提出了两种新的基于Cucurbit [7] uril（CB [7]）的催化剂循环策略，用于羟醛反应和鲁宾逊环化反应。这些回收方法在概念上是不同的。前者依赖于葫芦素中催化剂的均匀包封，CB [7]·Cat，并通过用有机溶剂萃取羟醛产物在水相中进行再循环。后者依赖于作为MNP-CB [7]·Cat2系统的催化剂的非均质封装，以及通过磁收回收的方法。密度泛函理论（DFT）计算已被用来合理化实验结果的热力学，并考虑到未来的催化设计提出了警告和合理的改进。
更新日期：2020-03-03
中文翻译：
评估超分子组装的有机催化物种的可回收性：理论上的见解。
不对称有机催化合成是有机化学中强大的工具，可通过温和的催化途径以高纯度获得所需的立体异构体。将均相催化物种固定在非均相上体现了不对称催化的发展，因为它允许催化剂循环运行几次直至降解。先前报道的将脯氨酸基催化剂用于醛醇缩合反应的非共价固定在用β-环糊精（MNP-β-CB）功能化的磁性纳米颗粒上证明了该方法的可行性。本文提出了两种新的基于Cucurbit [7] uril（CB [7]）的催化剂循环策略，用于羟醛反应和鲁宾逊环化反应。这些回收方法在概念上是不同的。前者依赖于葫芦素中催化剂的均匀包封，CB [7]·Cat，并通过用有机溶剂萃取羟醛产物在水相中进行再循环。后者依赖于作为MNP-CB [7]·Cat2系统的催化剂的非均质封装，以及通过磁收回收的方法。密度泛函理论（DFT）计算已被用来合理化实验结果的热力学，并考虑到未来的催化设计提出了警告和合理的改进。
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