Enantioselective C–C and C–heteroatom bond forming reactions using chiral ferrocene catalysts

Drusan, Michal; Šebesta, Radovan

doi:10.1016/j.tet.2013.11.012

Cited by 69 publications

(20 citation statements)

References 235 publications

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“…[63] Furthermore, it is a suitable candidate for magnetic circular dichroism [64] and, symmetrically, magnetoelectrochemistry experiments, [65] on account of the ferricinium j ferrocene Fc + j Fc redox couple including a paramagnetic species. Finally, chiral ferrocenes, including planar stereogenicity ones, gained great applicative interest in the field of asymmetric catalysis, [66][67][68][69][70][71][72][73][74][75][76][77][78] on account of attractive features including for example the great stability of the ferrocene group in air at ambient temperature, and of the above modulability of its electronic properties. In particular, in the last two decades, some of us have developed, characterized and/or tested many advanced ferrocene derivatives, [60,62,63] including planar-stereogenicity ferrocenes for stereoselective catalysis applications (e. g. [74,75] ).…”

Section: Introductionmentioning

confidence: 99%

Widening the Scope of “Inherently Chiral” Electrodes: Enantiodiscrimination of Chiral Electroactive Probes with Planar Stereogenicity

et al. 2020

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A series of planar‐stereogenicity ferrocenes, important as chiral promoters in enantioselective catalysis, is characterized in terms of relationships between structure and electronic properties. The enantiomers of six selected model cases are then successfully discriminated in voltammetry experiments on electrodes modified with electrodeposited inherently chiral oligomer films, in terms of significant potential differences, specular inverting probe or selector configuration. Small substituent changes do not alter the enantiomer peak sequence, but result in significant modulation of peak potential differences, which appear consistent with the availability of chiral/selector matching elements. The present stereogenic plane case, combined with former ones involving stereogenic centers, axes, and/or helices, shows that the inherent chirality strategy in electroanalysis can be effective with all four rigid stereogenic elements.

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Section: Introductionmentioning

confidence: 99%

Widening the Scope of “Inherently Chiral” Electrodes: Enantiodiscrimination of Chiral Electroactive Probes with Planar Stereogenicity

et al. 2020

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“…Nowadays, chiral ferrocene‐type compounds have been recognized as essential ligands/catalysts in both academic studies and industrial applications. Several excellent book chapters and reviews have been published in accord with the significance chiral ferrocenes …”

Section: Introductionmentioning

confidence: 99%

Chiral Oxazolinyl Hydroxyl Ferrocene Catalysts: Synthesis and Applications in Asymmetric Reactions

Zhang

Dai

2020

ChemistrySelect

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Chiral oxazolinyl hydroxyl ferrocenes have been demonstrated as representative catalysts in enantioselective nucleophilic addition reactions in the last few decades. They have received much interest from chemists because of not only the numerous substitution patterns at their sandwich backbones, but also their superior catalytic activity in asymmetric transformations. Recent research has revealed that the planar chirality of these catalysts influences the stereochemistry of asymmetric products and the application scope in enantioselective reactions. Herein, we provide an intensive survey of chiral oxazolinyl hydroxyl ferrocene compounds, including the structures of chiral compounds already published, designed synthetic approaches for ferrocenes with different patterns, and their utilization in the enantioselective preparation of secondary alcohols using organozinc reagents.

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“…Carbon‐carbon (C−C) and Carbon‐heteroatom (C−X) bond forming reactions are of great significance in organic chemistry. In our recent report, carbon‐heteroatom (C−Br) bond formation was applied on pyrazolyl enones (obtained from 4‐formylpyrazoles and acetone) to obtain new monobromo compounds which were utilized to synthesize bipyrazolyl compounds of antibacterial and antifungal interest .…”

Section: Introductionmentioning

confidence: 99%

Some New Pyrazolyl Pyrazolones and Cyanopyrazolyl Acrylates: Design, Synthesis and Biological Evaluation

et al. 2019

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The present work is aimed to report several new synthetically and medicinally important pyrazole derivatives. Herein, a series of new 3‐amino‐4‐((3‐aryl‐1‐phenyl‐1H‐pyrazol‐4‐yl) methylene)‐1H‐pyrazol‐5(4H)‐ones (4) were synthesized by the reaction of ethyl 2‐cyano‐3‐(3‐aryl‐1‐phenyl‐1H‐pyrazol‐4‐yl) acrylates (3) and hydrazine hydrate in good yields. All the fourteen compounds (3 and 4) were evaluated for the in vitro antibacterial activity against, Staphylococcus aureus and Bacillus subtilis (Gram Positive), Escherichia coli and Pseudomonas aeruginosa (Gram negative) and the antifungal activity against Candida albicans and Saccharomyces cerevisiae. The tested compounds were found to be active against both the Gram positive strains.

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Enantioselective C–C and C–heteroatom bond forming reactions using chiral ferrocene catalysts

Cited by 69 publications

References 235 publications

Widening the Scope of “Inherently Chiral” Electrodes: Enantiodiscrimination of Chiral Electroactive Probes with Planar Stereogenicity

Widening the Scope of “Inherently Chiral” Electrodes: Enantiodiscrimination of Chiral Electroactive Probes with Planar Stereogenicity

Chiral Oxazolinyl Hydroxyl Ferrocene Catalysts: Synthesis and Applications in Asymmetric Reactions

Some New Pyrazolyl Pyrazolones and Cyanopyrazolyl Acrylates: Design, Synthesis and Biological Evaluation

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