Enantioseparation and absolute configuration of the atropisomers of a naturally produced hexahalogenated 1,1′-dimethyl-2,2′-bipyrrole

Rosenfelder, Natalie; Ostrowicz, Patrizia; Fu, Liangfeng; Gribble, Gordon W.; Tittlemier, Sheryl A.; Frey, Wolfgang; Vetter, Walter

doi:10.1016/j.chroma.2010.01.083

Cited by 11 publications

(5 citation statements)

References 23 publications

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“…It is interesting to note that compound 3 due to its axial chirality could be separated by chiral HPLC into the stable atropisomers. 24 The spectroscopic data for the hexahalogenated 1,1¢-dimethyl-2,2¢bipyrroles 1-3 were in full agreement with those reported previously. 10,11a,23 In conclusion, the silver(I)-catalyzed pyrrole cyclization provides a facile access to 2,2¢-bipyrroles.…”

supporting

confidence: 89%

Transition Metals in Organic Synthesis, Part 97:¹ Silver-Catalyzed Synthesis of Hexahalogenated 2,2′-Bipyrroles

Martin¹,

Jäger²,

Knölker³

2011

Synlett

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confidence: 89%

Transition Metals in Organic Synthesis, Part 97:¹ Silver-Catalyzed Synthesis of Hexahalogenated 2,2′-Bipyrroles

Martin¹,

Jäger²,

Knölker³

2011

Synlett

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“…In this context, recently, biaryl synthetic analogues of hibarimicins have been enantioseparated on polysaccharide‐based CSPs by means of preparative HPLC and SFC . Vetter and co‐workers reported the semipreparative recovery of a group of polyhalogenated marino 2,2’‐bipyrroles to perform X‐ray diffraction analyses to determine the absolute configuration . Mancinelli and co‐workers reported the semipreparative enantioseparation of an atropisomeric azaborine on Chiralpak AS‐H and determined the absolute configuration by comparison of experimental and theoretical CD spectra .…”

Section: Liquid‐phase Enantioseparation Of Stable Atropisomersmentioning

confidence: 99%

Recent trends and applications in liquid‐phase chromatography enantioseparation of atropisomers

et al. 2017

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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.

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“…Pure atropisomers can be obtained only by separating racemic mixtures of synthesized compounds and, for this purpose, HPLC methods can play a key role in the research plan development. In our previous work, the HPLC technique was used to enantioseparate atropisomeric 3,3′‐dibromo‐5,5′‐disubstituted‐4,4′‐bipyridines at multimilligram scale by using both cellulose‐ and amylose‐based chiral columns belonging to the series Chiralcel, Chiralpak, and Lux, which are known to efficiently enantioseparate molecular systems featuring a chiral axis as exclusive source of molecular dissymmetry . It was found that due to the high aromatic character of the analyzed 4,4′‐bipyridines, hydrophobic π–π interactions deeply contribute to the recognition mechanism both in normal‐phase liquid chromatography (NPLC) and polar organic solvent chromatography (POSC) elution modes.…”

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confidence: 99%

High‐performance liquid chromatography enantioseparation of polyhalogenated 4,4′‐bipyridines on polysaccharide‐based chiral stationary phases under multimodal elution

Peluso

Mamane

Aubert

et al. 2014

J of Separation Science

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An investigation on the high-performance liquid chromatography enantioseparation of 12 polyhalogenated 4,4'-bipyridines on polysaccharide-based chiral stationary phases is described. The overall study was directed toward the generation of efficient separations in order to obtain pure atropisomers that will serve as ligands for building homochiral metal organic frameworks. Four coated columns--namely, Lux Cellulose-1, Lux Cellulose-2, Lux Cellulose-4, and Lux Amylose-2--and two immobilized columns--namely, Chiralpak IC and IA--were used under normal, polar organic, and reversed-phase elution modes. Moreover, Chiralcel OJ was considered under normal-phase and polar organic conditions. The effect of the chiral selector and mobile phase composition on the enantioseparation, the enantiomer elution order and the beneficial effect of nonstandard solvents were studied. The effect of water in the mobile phase on the enantioselectivity and retention was investigated and retention profiles typical of hydrophilic interaction liquid chromatography were observed. Interesting phenomena of solvent-induced enantiomer elution order reversal occurred under normal-phase mode. All the considered 4,4'-bipyridines were enantioseparated at the multimilligram level.

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Enantioseparation and absolute configuration of the atropisomers of a naturally produced hexahalogenated 1,1′-dimethyl-2,2′-bipyrrole

Cited by 11 publications

References 23 publications

Transition Metals in Organic Synthesis, Part 97:¹ Silver-Catalyzed Synthesis of Hexahalogenated 2,2′-Bipyrroles

Transition Metals in Organic Synthesis, Part 97:¹ Silver-Catalyzed Synthesis of Hexahalogenated 2,2′-Bipyrroles

Recent trends and applications in liquid‐phase chromatography enantioseparation of atropisomers

High‐performance liquid chromatography enantioseparation of polyhalogenated 4,4′‐bipyridines on polysaccharide‐based chiral stationary phases under multimodal elution

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