Separation of enantiomers: needs, challenges, perspectives

Maier, Norbert M.; Franco, Pilar; Lindner, Wolfgang

doi:10.1016/s0021-9673(00)00532-x

Cited by 965 publications

(736 citation statements)

References 204 publications

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“…A full list of chemicals used in this study and their sources can be found in SI Appendix. The full synthesis procedure for the chiral SDA used in this study as well as the respective 1 H and 13 C NMR characterization data are described in detail in SI Appendix.…”

Section: Methodsmentioning

confidence: 99%

“…Despite the abundance of chirality in nature, the discovery of a zeolite or zeolite-like microporous material with enantioselective properties has remained elusive. Enantioenriched, chiral zeolitic materials are of particular interest for their potential to provide robust, new, enantiospecific, shape-selective catalytic pathways and separation processes (6)(7)(8)(9)(10)(11)(12)(13).…”

mentioning

confidence: 99%

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Enantiomerically enriched, polycrystalline molecular sieves

Brand

Schmidt

Deem

et al. 2017

Proc. Natl. Acad. Sci. U.S.A.

116

140

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Zeolite and zeolite-like molecular sieves are being used in a large number of applications such as adsorption and catalysis. Achievement of the long-standing goal of creating a chiral, polycrystalline molecular sieve with bulk enantioenrichment would enable these materials to perform enantioselective functions. Here, we report the synthesis of enantiomerically enriched samples of a molecular sieve. Enantiopure organic structure directing agents are designed with the assistance of computational methods and used to synthesize enantioenriched, polycrystalline molecular sieve samples of either enantiomer. Computational results correctly predicted which enantiomer is obtained, and enantiomeric enrichment is proven by high-resolution transmission electron microscopy. The enantioenriched and racemic samples of the molecular sieves are tested as adsorbents and heterogeneous catalysts. The enantioenriched molecular sieves show enantioselectivity for the ring opening reaction of epoxides and enantioselective adsorption of 2-butanol (the R enantiomer of the molecular sieve shows opposite and approximately equal enantioselectivity compared with the S enantiomer of the molecular sieve, whereas the racemic sample of the molecular sieve shows no enantioselectivity). chirality | zeolite | asymmetric catalysis | chiral adsorption

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Section: Methodsmentioning

confidence: 99%

mentioning

confidence: 99%

Enantiomerically enriched, polycrystalline molecular sieves

Brand

Schmidt

Deem

et al. 2017

Proc. Natl. Acad. Sci. U.S.A.

116

140

View full text Add to dashboard Cite

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“…therapeutic or harmful). 1 In the late 1950s, the racemic mixture of Thalidomide, for example, was widely prescribed to relieve the symptoms of morning sickness in pregnant women. Nevertheless, the drug was withdrawn in 1962 after a birth defects crisis, where it was later discovered that the (R) enantiomer is effective against morning sickness while the (S) enantiomer causes birth defects.…”

mentioning

confidence: 99%

“…These two methods, though commonly used to obtain single enantiomers, have three disadvantages: (i) Separation by HPLC require expensive instrumentation and stationary phase. 1 (ii) A particular chiral stationary phase may only work for a limited number of compounds. 6,7 (iii) Formation of diastereomers introduces another compound into the system, and requires additional crystallization and filtration steps.…”

mentioning

confidence: 99%

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Separation and enrichment of enantiopure from racemic compounds using magnetic levitation

et al. 2014

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Chiral Pharmaceuticals

Tiritan

Ribeiro

Fernandes

et al. 2016

Kirk-Othmer Encyclopedia of Chemical Technology

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The implication of chirality in pharmaceuticals is briefly reviewed, presenting the basic concepts and the chiral recognition phenomenon in biological systems. The importance to recognize enantiomers of chiral pharmaceuticals, both in pharmacology and environmental fields, is emphasized and many examples were selected to demonstrate the significance of chirality in both areas. Methodologies to obtain single enantiomers and to control the enantiomeric fraction associated with enantioseparation of chiral pharmaceuticals are also discussed. Several enantioselective methods using liquid chromatography (LC) with chiral stationary phases (CSPs) in biomedical and environmental fields are presented. The most used CSPs, their advantages and drawbacks, are swiftly revised.

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Separation of enantiomers: needs, challenges, perspectives

Cited by 965 publications

References 204 publications

Enantiomerically enriched, polycrystalline molecular sieves

Enantiomerically enriched, polycrystalline molecular sieves

Separation and enrichment of enantiopure from racemic compounds using magnetic levitation

Chiral Pharmaceuticals

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