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Relevant academic research and scientific papers

A High Loading and Recyclable Pentaerythritol Supported Imidazolidin-4-one Catalyst for Enantioselective Diels–Alder Reactions

Abstract: The synthesis of high loading and recyclable pentaerythritol supported imidazolidin-4-one catalyst I and its application in enantioselective Diels–Alder reactions of cyclopentadiene and α,β-unsaturated aldehydes with high performance were descri

Non-Covalently Immobilized Chiral Imidazolidinone on Sulfated-Chitin: Reusable Heterogeneous Organocatalysts for Asymmetric Diels-Alder Reaction

A heterogeneous chiral imidazolodinone catalyst was synthesized by immobilization on a sulfated chitin through non-covalent ionic interactions. The chitin-based organocatalyst promoted the asymmetric Diels-Alder reaction with high enantioselectivity under heterogeneous conditions and was successfully reused multiple times without apparent loss of catalytic activity and enantioselectivity.

Chiral Imidazolidin-4-one with catalytic amount of Dicationic ionic liquid act as a recoverable and reusable Organocatalyst for asymmetric Diels-Alder reaction

Imidazolidin-4-one is used as a recoverable organocatalyst for the asymmetric Diels-Alder reaction in the presence of catalytic amount of dicationic ionic liquid and trifluoroacetic acid as a co-catalyst. The Diels-Alder reaction between model substrate cyclopentadiene and crotonaldehyde gave the product in 95% conversion and 87% ee of the endo-product. The catalyst was shown better reusability when the 20?mol% of dicationic ionic liquid was used and catalyst was reused upto 5 cycles, conversion remains upto 3 recycles but ee of endo-9 was slightly droped.

Enantioselective Organocatalytic Enamine C?H Oxidation/Diels- Alder Reaction

α,β-unsaturated aldehydes have been traditionally used in LUMO lowering asymmetric aminocatalysis (iminium catalysis), while the use of saturated aldehydes as substrates in this type of catalysis has been elusive, until recently. Herein, we demonstrate that organic, single-electron oxidants in the presence of diarylprolinol silylether type catalysts serve as effective tools for the transformation of electron rich enamines to iminium ions which partake in a subsequent Diels-Alder reaction. This enantioselective one-pot transformation represents the first example of saturated aldehydes being used in domino Diels-Alder reaction processes and demonstrates the power of this protocol for construction of stereo-defined chiral compounds and building blocks. (Figure presented.).

Novel binaphthyl and biphenyl α- and β-amino acids and esters: organocatalysis of asymmetric Diels-Alder reactions. A combined synthetic and computational study

Asymmetric catalysis of the Diels-Alder reaction between cyclopentadiene and cinnamaldehydes has been studied using as catalysts a range of novel α- and β-aminoacids and aminoesters with binaphthyl and biphenyl backbones, providing enantioselectivities of

Chiral GAP catalysts of phosphonylated imidazolidinones and their applications in asymmetric Diels-Alder and Friedel-Crafts reactions

The design and synthesis of recyclable imidazolidinone catalysts using GAP chemistry/technique was described. Their applications in asymmetric Diels-Alder and Friedel-Crafts reactions with α,β-unsaturated aldehydes resulted in excellent yields and higher enantioselectivities than previous processes. As recyclable small molecular catalysts, phosphonylated imidazolidinones can be recovered and reused for up to three runs without costing significant decrease in catalytic activity.

Caveat in the stereochemical outcome of the organocatalytic Diels-Alder reaction in PEG-400

The organocatalytic Diels-Alder reaction in non-conventional solvent (PEG-400) has yielded cycloaddition products with diastereoselectivities hitherto not reported in detail using classical reaction conditions.

New insights into the asymmetric Diels-Alder reaction: The endo- and S-selective retro-Diels-Alder reaction

The endo- and S-selective retro-Diels-Alder reactions in an imidazolethione-catalyzed asymmetric Diels-Alder reaction were verified and investigated, and account for the low ee values in a CH3CN-H2O catalytic system. This reverse pro

Synthesis of MacMillan catalyst modified with ionic liquid as a recoverable catalyst for asymmetric Diels-Alder reaction

MacMillan catalyst was modified with imidazolium ionic liquid by ester linkage and acts as recoverable and reusable catalyst for asymmetric Diels-Alder reactions. A Diels-Alder reaction between cyclopentadiene and crotonaldehyde was carried out using MacMillan catalyst modified with ionic liquid (5 mol%) using trifluoroacetic acid (5 mol%) as co-catalyst in acetonitrile-water (95 : 5) at room temperature, to give 94% conversion of Diels-Alder adduct with exo/endo (1 : 1.1) and 90% ee of endo product. The catalyst was recovered and reused up to 5 cycles with a slight decrease in ee and product conversion.

Improving catalyst activity in secondary amine catalysed transformations

The effect on catalyst performance of altering substituents at the 2-position of the Macmillan imidazolidinone has been examined. Condensation of l-phenylalanine N-methyl amide with acetophenone derivatives results in a series of imidazolidinones whose sa