ON/OFF receptor-like enantioseparation of planar chiral 1,2-ferrocenes on an amylose-based chiral stationary phase: The role played by 2-propanol

Cantatore, Chiara; Korb, Marcus; Lang, Heinrich; Cirilli, Roberto

doi:10.1016/j.aca.2022.339880

Cited by 8 publications

(11 citation statements)

References 33 publications

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“…Analytes 1-14 feature halogen atoms (1-3 and 7-14), methyl (4) and aromatic (5,6) groups as substituents of 1,2-and 1,3-disubstituted ferrocene scaffolds. The recognition site pattern of these compounds was explored by V analysis (Supporting Information, Tables S3 and S4) [4,5].…”

Section: Resultsmentioning

confidence: 99%

“…S5). This trend may suggest that the Ph substituent of 5 participates more efficiently in π-π interactions than the larger 2-naphthyl substituent (6) which is more prone to fill the hydrophobic cavity of the CSP with MeOH-containing MPs. On the other hand, for ferrocenes 4-6, the impact of the substituent on the enantioseparation depended on the elution mode.…”

Section: Chromatographic Screeningmentioning

confidence: 99%

“…This is particularly true for halogenated planar chiral ferrocenes given that they are versatile and valuable intermediates to access chiral ferrocenes with various functionalities [14][15][16]. On the other hand, studies on the enantioseparation of new chiral compounds may enable to acquire information on unusual and new chiral recognition mechanisms and related noncovalent interactions [5,6].…”

Section: Introductionmentioning

confidence: 99%

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Enantioseparation of planar chiral ferrocenes on cellulose‐based chiral stationary phases: Benzoate versus carbamate pendant groups

et al. 2022

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Section: Resultsmentioning

confidence: 99%

Section: Chromatographic Screeningmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Enantioseparation of planar chiral ferrocenes on cellulose‐based chiral stationary phases: Benzoate versus carbamate pendant groups

et al. 2022

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“…Moreover, for a long time the preparation of pure enantiomers of certain planar chiral ferrocenes, for instance those containing a pyridine core, required diastereomeric resolution or enantioselective high-performance liquid chromatography (HPLC) separation [38,43]. However, despite the growing interest in planar chiral ferrocenes containing only a chiral plane as a stereogenic unit (Figure 4A, B), the enantioseparation of this type of compounds was not comprehensively explored, and very few systematic analytical studies were reported so far [44][45][46][47][48]. On the other F I G U R E 4 Chiral ferrocene motifs studied in enantioseparation science (R 1 * = chiral framework): planar chiral ferrocenes containing only a chiral plane as a stereogenic unit (A,B); chiral ferrocenes featured by a single chiral centre as a stereogenic unit (C); planar chiral ferrocenes featured by both central and planar chirality (D) hand, enantioselective HPLC has been frequently used in organic and organometallic chemistry studies in order to measure the enantiomeric purity of planar chiral ferrocenes prepared by asymmetric synthesis.…”

Section: Introductionmentioning

confidence: 99%

Ferrocene derivatives with planar chirality and their enantioseparation by liquid‐phase techniques

Peluso

Mamane

2022

Electrophoresis

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In the last decade, planar chiral ferrocenes have attracted a growing interest in several fields, particularly in asymmetric catalysis, medicinal chemistry, chiroptical spectroscopy and electrochemistry. In this frame, the access to pure or enriched enantiomers of planar chiral ferrocenes has become essential, relying on the availability of efficient asymmetric synthesis procedures and enantioseparation methods. Despite this, in enantioseparation science, these metallocenes were not comprehensively explored, and very few systematic analytical studies were reported in this field so far. On the other hand, enantioselective highperformance liquid chromatography has been frequently used by organic and organometallic chemists in order to measure the enantiomeric purity of planar chiral ferrocenes prepared by asymmetric synthesis. On these bases, this review aims to provide the reader with a comprehensive overview on the enantioseparation of planar chiral ferrocenes by discussing liquid-phase enantioseparation methods developed over time, integrating this main topic with the most relevant aspects of ferrocene chemistry. Thus, the main structural features of ferrocenes and the methods to model this class of metallocenes will be briefly summarized. In addition, planar chiral ferrocenes of applicative interest as well as the limits of asymmetric synthesis for the preparation of some classes of planar chiral ferrocenes will also be discussed with the aim to orient analytical scientists towards 'hot topics' and issues which are still open for accessing enantiomers of ferrocenes featured by planar chirality.

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“…One strategy for the development of new pieces of knowledge on the mechanistic aspect of the enantioseparation process is the design of tailored chiral probes that display a chromatographic behavior traceable to specific structural elements [ 12 , 13 , 14 , 15 , 16 , 17 , 18 , 19 , 20 ]. This approach allows the construction of reliable structure–enantioselectivity relationships and, indirectly, the identification of the key portions of the selector involved in the enantioseparation.…”

Section: Introductionmentioning

confidence: 99%

HPLC Enantioseparation of Rigid Chiral Probes with Central, Axial, Helical, and Planar Stereogenicity on an Amylose (3,5-Dimethylphenylcarbamate) Chiral Stationary Phase

Rizzo¹,

Benincori

Fontana

et al. 2022

Molecules

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The chiral resolving ability of the commercially available amylose (3,5-dimethylphenylcarbamate)-based chiral stationary phase (CSP) toward four chiral probes representative of four kinds of stereogenicity (central, axial, helical, and planar) was investigated. Besides chirality, the evident structural feature of selectands is an extremely limited conformational freedom. The chiral rigid analytes were analyzed by using pure short alcohols as mobile phases at different column temperatures. The enantioselectivity was found to be suitable for all compounds investigated. This evidence confirms that the use of the amylose-based CSP in HPLC is an effective strategy for obtaining the resolution of chiral compounds containing any kind of stereogenic element. In addition, the experimental retention and enantioselectivity behavior, as well as the established enantiomer elution order of the investigated chiral analytes, may be used as key information to track essential details on the enantiorecognition mechanism of the amylose-based chiral stationary phase.

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ON/OFF receptor-like enantioseparation of planar chiral 1,2-ferrocenes on an amylose-based chiral stationary phase: The role played by 2-propanol

Cited by 8 publications

References 33 publications

Enantioseparation of planar chiral ferrocenes on cellulose‐based chiral stationary phases: Benzoate versus carbamate pendant groups

Enantioseparation of planar chiral ferrocenes on cellulose‐based chiral stationary phases: Benzoate versus carbamate pendant groups

Ferrocene derivatives with planar chirality and their enantioseparation by liquid‐phase techniques

HPLC Enantioseparation of Rigid Chiral Probes with Central, Axial, Helical, and Planar Stereogenicity on an Amylose (3,5-Dimethylphenylcarbamate) Chiral Stationary Phase

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