Comparative enantioseparation of planar chiral ferrocenes on polysaccharide‐based chiral stationary phases

Autor:	Alessandro Dessì, Barbara Sechi, Roberto Dallocchio, Bezhan Chankvetadze, Mireia Pérez‐Baeza, Sergio Cossu, Victor Mamane, Patrick Pale, Paola Peluso
Rok vydání:	2022
Předmět:	Pharmacology Planar chirality Metallocenes Electrostatic potential electrostatic potential enantioseparation ferrocenes planar chirality polysaccharide-based chiral stationary phases Organic Chemistry Stereoisomerism Química analítica Settore CHIM/06 - Chimica Organica Polysaccharide-based chiral stationary phases Catalysis Enantioseparation Analytical Chemistry Polysaccharides Drug Discovery Settore CHIM/01 - Chimica Analitica Amylose Ferrocenes Chromatography High Pressure Liquid Spectroscopy
Zdroj:	Chirality (N.Y.N.Y., Online) (2022). doi:10.1002/chir.23417 info:cnr-pdr/source/autori:Alessandro Dessì, Barbara Sechi, Roberto Dallocchio, Bezhan Chankvetadze, Mireia Pérez-Baeza, Sergio Cossu, Victor Mamane, Patrick Pale, Paola Peluso/titolo:Comparative enantioseparation of planar chiral ferrocenes on polysaccharide-based chiral stationary phases/doi:10.1002%2Fchir.23417/rivista:Chirality (N.Y.N.Y., Online)/anno:2022/pagina_da:/pagina_a:/intervallo_pagine:/volume Dessì, Alessandro Sechi, Barbara Dallocchio, Roberto Chankvetadze, Bezhan Pérez Baeza, Mireia Cossu, Sergio Mamane, Victor Pale, Patrick Peluso, Paola 2022 Comparative enantioseparation of planar chiral ferrocenes on polysaccharide-based chiral stationary phases. Chirality 34 4 609 619
ISSN:	1520-636X 0899-0042
DOI:	10.1002/chir.23417
Popis:	Planar chiral ferrocenes are well-known compounds that have attracted interest for application in synthesis, catalysis, material science, and medicinal chemistry for several decades. In spite of the fact that asymmetric synthesis procedures for obtaining enantiomerically enriched ferrocenes are available, sometimes, the accessible enantiomeric excess of the chiral products is unsatisfactory. In such cases and for resolution of racemic planar chiral ferrocenes, enantioselective high-performance liquid chromatography (HPLC) on polysaccharide-based chiral stationary phases (CSPs) has been used in quite a few literature articles. However, although moderate/high enantioselectivities have been obtained for planar chiral ferrocenes bearing polar substituents, the enantioseparation of derivatives containing halogens, or exclusively alkyl groups, remains rather challenging. In this study, the enantioseparation of ten planar chiral 1,2- and 1,3-disubstituted ferrocenes was explored by using five polysaccharide-based CSPs under multimodal elution conditions. Baseline enantioseparations were achieved for nine analytes with separation factors (alfa) ranging from 1.20 to 2.92. The presence of pai-extended systems in the analyte structure was shown to impact affinity of the most retained enantiomer toward amylose-based selectors, observing retention times higher than 80 min with methanol-containing mobile phases (MPs). Electrostatic potential (V) analysis and molecular dynamics (MD) simulations were used in order to study interaction modes at the molecular level.
Databáze:	OpenAIRE
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