Silica gel-immobilised chiral 1,2-benzenedisulfonimide: a Brønsted acid heterogeneous catalyst for enantioselective multicomponent Passerini reaction

Antenucci, Achille; Marra, Francesco; Dughera, Stefano

doi:10.1039/d1ra05297g

Cited by 12 publications

(12 citation statements)

References 71 publications

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“… Preparation of the U/CC@silica gel ( 17 ); b) Passerini reaction of the isocyanide, aldehyde or ketone and carboxylic acid using catalyst [95] …”

Section: Catalyst On Silica Support Matrix For Organic Transformationsmentioning

confidence: 99%

“…Preparation of the U/CC@silica gel (17); b) Passerini reaction of the isocyanide, aldehyde or ketone and carboxylic acid using catalyst. [95] ChemistrySelect (34). During this reaction, L-proline generates a chiral enamine, which then adds to the aldehyde (33) C=O bond, leading eventually to the (S)-configured aldol (Scheme 5).…”

Section: Catalyst On Silica-gel Support For Chiral Organic Transforma...mentioning

confidence: 99%

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Porous Silica Support for Immobilizing Chiral Metal Catalyst: Unravelling the Activity of Catalyst on Asymmetric Organic Transformations

2022

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The role of chiral metal catalysts in asymmetric reactions has developed a new forte for researchers worldwide to boost chiral synthesis in various sectors. By controlling specific interactions among chiral ligands, metal catalysts and the support material, one can design a more selective and efficient chiral heterogeneous catalytic system. Silica has been extensively used as support material in various heterogeneous systems due to its activity, stability, better recovery, and recyclability. This review details recent advances in preparation of the silica suppported chiral catalysts and their applications for various chiral transformatios such as Aldol reaction, Henry reaction, transfer hydrogenation, epoxidation, Passerini reaction etc. The review also covers different mechanisms of immobilization viz., adsorption, electrostatic and covalent interactions. The interaction mechanism of chiral metal catalyst with silica support and factors like matrix pore size and ligand confinement that influence the catalytic performance of enantioselective transformations have also been discussed.

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“… Preparation of the U/CC@silica gel ( 17 ); b) Passerini reaction of the isocyanide, aldehyde or ketone and carboxylic acid using catalyst [95] …”

Section: Catalyst On Silica Support Matrix For Organic Transformationsmentioning

confidence: 99%

Section: Catalyst On Silica-gel Support For Chiral Organic Transforma...mentioning

confidence: 99%

Porous Silica Support for Immobilizing Chiral Metal Catalyst: Unravelling the Activity of Catalyst on Asymmetric Organic Transformations

2022

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“…One exception for enantioselective heterogeneous-catalyzed MCRs is the recently published work of Dughera and co-workers [ 222 ]. In their work, a chiral benzenedisulfonimide derivative was immobilized with 3-aminopropyl functionalized silica gel, affording the heterogeneous catalyst, which was successfully applied in an enantioselective version of the Passerini reaction ( Scheme 17 ).…”

Section: Homogeneous and Heterogeneous Catalysismentioning

confidence: 99%

“…Several solvents and conditions were tested, but the reaction performed better using a deep eutectic mixture (urea/choline chloride) [ 222 ]. Numerous derivatives could be obtained with high yields (78–93%) and enantiomeric excesses (up to 92% for all substrates).…”

Section: Homogeneous and Heterogeneous Catalysismentioning

confidence: 99%

“…Five cycles could be carried out, and both yields and enantiomeric excesses remained similar to those in the first cycle (i.e., nearly 95 and 94%, respectively). This work [ 222 ] certainly represents a huge advance in the use of heterogeneous catalysis to perform enantioselective MCRs. The limited number of available catalysts to carry out enantioselective multicomponent transformations under heterogeneous conditions is strongly indicative of challenges in the development of these catalytic systems.…”

Section: Homogeneous and Heterogeneous Catalysismentioning

confidence: 99%

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Catalytic Approaches to Multicomponent Reactions: A Critical Review and Perspectives on the Roles of Catalysis

2021

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In this review, we comprehensively describe catalyzed multicomponent reactions (MCRs) and the multiple roles of catalysis combined with key parameters to perform these transformations. Besides improving yields and shortening reaction times, catalysis is vital to achieving greener protocols and to furthering the MCR field of research. Considering that MCRs typically have two or more possible reaction pathways to explain the transformation, catalysis is essential for selecting a reaction route and avoiding byproduct formation. Key parameters, such as temperature, catalyst amounts and reagent quantities, were analyzed. Solvent effects, which are likely the most neglected topic in MCRs, as well as their combined roles with catalysis, are critically discussed. Stereocontrolled MCRs, rarely observed without the presence of a catalytic system, are also presented and discussed in this review. Perspectives on the use of catalytic systems for improved and greener MCRs are finally presented.

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Design, Synthesis and Application of C₂‐Symmetric Cycloglycerodiphosphate Catalysts

et al. 2023

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Chiral phosphoric acids (CPAs) and their salts are the privileged catalysts in a plethora of asymmetric transformations. All of the scaffolds of efficient CPAs rely on C2‐symmetry and axial chirality, while the only examples of punctually chiral CPAs are TADDOL derivatives. Herein, we present the design and the synthesis of C2‐symmetric cycloglycerophosphates (cGPAs) and their application throughout the addition of trimethylsilyl cyanide (TMSCN) to aldehydes and ketones, to obtain the corresponding cyanohydrins in yields between 77 and 99% and ee between 84.2 and 99.5% (27 examples). A DFT computational model is moreover performed to rationalize the reaction mechanism and its stereochemical outcome.

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Silica gel-immobilised chiral 1,2-benzenedisulfonimide: a Brønsted acid heterogeneous catalyst for enantioselective multicomponent Passerini reaction

Abstract: A chiral heterogeneous catalyst derivative of (−)-4,5-dimethyl-3,6-bis(1-naphthyl)-1,2-benzenedisulfonimide is proven here to be efficient in a three-component asymmetric Passerini protocol, carried out in a deep eutectic solvent.

Cited by 12 publications

References 71 publications

Porous Silica Support for Immobilizing Chiral Metal Catalyst: Unravelling the Activity of Catalyst on Asymmetric Organic Transformations

Porous Silica Support for Immobilizing Chiral Metal Catalyst: Unravelling the Activity of Catalyst on Asymmetric Organic Transformations

Catalytic Approaches to Multicomponent Reactions: A Critical Review and Perspectives on the Roles of Catalysis

Design, Synthesis and Application of C₂‐Symmetric Cycloglycerodiphosphate Catalysts

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Silica gel-immobilised chiral 1,2-benzenedisulfonimide: a Brønsted acid heterogeneous catalyst for enantioselective multicomponent Passerini reaction

Abstract: A chiral heterogeneous catalyst derivative of (−)-4,5-dimethyl-3,6-bis(1-naphthyl)-1,2-benzenedisulfonimide is proven here to be efficient in a three-component asymmetric Passerini protocol, carried out in a deep eutectic solvent.

Cited by 12 publications

References 71 publications

Porous Silica Support for Immobilizing Chiral Metal Catalyst: Unravelling the Activity of Catalyst on Asymmetric Organic Transformations

Porous Silica Support for Immobilizing Chiral Metal Catalyst: Unravelling the Activity of Catalyst on Asymmetric Organic Transformations

Catalytic Approaches to Multicomponent Reactions: A Critical Review and Perspectives on the Roles of Catalysis

Design, Synthesis and Application of C2‐Symmetric Cycloglycerodiphosphate Catalysts

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Design, Synthesis and Application of C₂‐Symmetric Cycloglycerodiphosphate Catalysts