Recent trends and applications in liquid-phase chromatography enantioseparation of atropisomers.
The term Atropisomerism defines a type of enantiomerism that arises from hindered rotation around an axis that makes two rotational isomers enantiomers. Atropisomeric compounds are present in nature, being important building blocks of many biologically active compounds. Atropisomers have been extensively studied in environmental and toxicological chemistry and, in particular, separating them has become a need in specific fields as organic synthesis and pharmaceutical research. High-performance LC has been fruitfully applied in this context, and despite HPLC separation on chiral stationary phase is considered as mature technology nowadays, in the last years several advancements and applications contributed to study compounds where axial chirality is of utmost importance. Moreover, dynamic chromatography has been exploited as a versatile tool for kinetic studies of systems with slow internal motion gaining essential information on their stereodynamic behavior. On this basis, current topics and trends in liquid-phase chromatography enantioseparation of atropisomers are presented herein with specific focus on new representative applications with HPLC, covering years 2010-2016. Some examples concerning supercritical fluid chromatography applications are also reported. This review aims to provide the reader with a modern overview of the field to highlight the renewed interest toward the chemistry of molecules with atropisomeric properties. A systematic compilation of all published literature has not been attempted.
Istituto di Chimica Biomolecolare ICB CNR - Sede Secondaria di Sassari, Sassari, Italy.
Paola
P
Peluso
Institut de Chimie de Strasbourg, UMR CNRS, Strasbourg Cedex, France.
Victor
V
Mamane
Cristallographie, Résonance Magnétique et Modélisations (CRM2), UMR CNRS, Université de Lorraine, Vandoeuvre-les-Nancy, France.
Emmanuel
E
Aubert
Dipartimento di Scienze Molecolari e Nanosistemi, Università Ca' Foscari di Venezia, Mestre Venezia, Italy.
Sergio
S
Cossu
D002851:Chromatography, High Pressure Liquid / Q000379:methods*; D025924:Chromatography, Supercritical Fluid; D013237:Stereoisomerism
Atropisomerism; Chiral stationary phase; Dynamic chromatography; Enantioseparation; HPLC