Polymer Supported Proline-Based Organocatalysts in Asymmetric Aldol
Reactions: A Review

Rubina, Shajahan; Rithwik, Sarang; Anas, S.

doi:10.2174/2213337209666220112094231

Cited by 7 publications

(2 citation statements)

References 69 publications

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“…The supported/immobilized/ heterogeneous catalysts were considered beyond the scope of this survey of the literature, because the structural modifications are aimed at the catalyst's recovery and reuse. Readers are kindly addressed to specific reviews covering the topic of pyrrolidine-based recyclable organocatalysts [21][22][23][24][25][26].…”

Section: Introductionmentioning

confidence: 99%

Recent Advances in Asymmetric Synthesis of Pyrrolidine-Based Organocatalysts and Their Application: A 15-Year Update

2023

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In 1971, chemists from Hoffmann-La Roche and Schering AG independently discovered a new asymmetric intramolecular aldol reaction catalyzed by the natural amino acid proline, a transformation now known as the Hajos–Parrish–Eder–Sauer–Wiechert reaction. These remarkable results remained forgotten until List and Barbas reported in 2000 that L-proline was also able to catalyze intermolecular aldol reactions with non-negligible enantioselectivities. In the same year, MacMillan reported on asymmetric Diels–Alder cycloadditions which were efficiently catalyzed by imidazolidinones deriving from natural amino acids. These two seminal reports marked the birth of modern asymmetric organocatalysis. A further important breakthrough in this field happened in 2005, when Jørgensen and Hayashi independently proposed the use of diarylprolinol silyl ethers for the asymmetric functionalization of aldehydes. During the last 20 years, asymmetric organocatalysis has emerged as a very powerful tool for the facile construction of complex molecular architectures. Along the way, a deeper knowledge of organocatalytic reaction mechanisms has been acquired, allowing for the fine-tuning of the structures of privileged catalysts or proposing completely new molecular entities that are able to efficiently catalyze these transformations. This review highlights the most recent advances in the asymmetric synthesis of organocatalysts deriving from or related to proline, starting from 2008.

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Section: Introductionmentioning

confidence: 99%

Recent Advances in Asymmetric Synthesis of Pyrrolidine-Based Organocatalysts and Their Application: A 15-Year Update

2023

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“…Several studies reported on the successful application of aminated polymers and polymer resins as aldol condensation catalysts [1,[24][25][26][27][28][29][30][31]. As support material, the polymer backbone can offer sufficient tolerance against problematic degradation reactions, as such contributing to enhanced catalytic stability and reusability.…”

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confidence: 99%

A Pyrrolidine Functionalized Poly[(ethylene glycol) Methacrylate] Resin as a Heterogeneous Catalyst for Aqueous Aldol Reactions

et al. 2022

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The development of a performant aminated catalyst for aldol condensations requires the combined tuning of the active site, support and solvent system. For this purpose, a pyrrolidine group was immobilized on a swellable polymer resin. Favorable interactions between the support and water (in its role as solvent) resulted in a turnover frequency (TOF) amounting to 3.0 ± 1.5·10−3 s−1, despite potential inhibition of the active sites by formation of iminium species. The affinity of the solvent for the poly[(ethylene glycol) methacrylate] support resulted in efficient swelling of the catalytic material, which was shown to be key to the observed catalytic performance.

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Proline‐Functionalized Magnetic Nanoparticles as Highly Performing Asymmetric Catalysts

Álvarez‐Bermúdez,

Landfester,

Zhang

et al. 2024

Macromol. Rapid Commun.

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Amino acids have a crucial role in the field of asymmetric organocatalysis for the production of chiral compounds with high added value and specific biological activity. In particular, proline offers high activity and stereoselectivity for catalyzing aldol reactions in organic solvents. However, proline‐based catalysts often lack water‐solubility, accessibility, catalytic performance, or recovery in aqueous media. This work reports the design of proline‐functionalized poly(methyl methacrylate) (PMMA) nanoparticles with a magnetic core that offer high availability of chiral units in water and high recyclability. A proline‐based copolymerizable surfactant is designed and integrated onto the surface of PMMA nanoparticles through a miniemulsion polymerization process without using additional surfactants. The miniemulsion technique allows the incorporation of magnetite to the system to create a magnetically separable catalyst. The chiral nanocatalyst presents a high diastereoselective catalytic activity for the intermolecular aldol reaction between p‐nitrobenzaldehyde and cyclohexanone in water.

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Polymer Supported Proline-Based Organocatalysts in Asymmetric Aldol Reactions: A Review

Cited by 7 publications

References 69 publications

Recent Advances in Asymmetric Synthesis of Pyrrolidine-Based Organocatalysts and Their Application: A 15-Year Update

Recent Advances in Asymmetric Synthesis of Pyrrolidine-Based Organocatalysts and Their Application: A 15-Year Update

A Pyrrolidine Functionalized Poly[(ethylene glycol) Methacrylate] Resin as a Heterogeneous Catalyst for Aqueous Aldol Reactions

Proline‐Functionalized Magnetic Nanoparticles as Highly Performing Asymmetric Catalysts

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