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Separation of 4C-Substituted Pyrrolidin-2-One Derivatives on Polysaccharide-Based Coated Chiral Stationary Phases

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Abstract

Fifteen structurally different 4C-substituted pyrrolidin-2-one derivatives were used as model analytes for investigation of enantioseparation abilities on six commercially available polysaccharide-based coated chiral stationary phases (cellulose tris (3,5-dimethylphenylcarbamate), cellulose tris (3-chloro-4-methylphenylcarbamate), cellulose tris (4-methylbenzoate), cellulose tris (4-chloro-3-methylphenylcarbamate), amylose tris (3,5-dimethylphenylcarbamate), and amylose tris (5-chloro-2-methylphenylcarbamate) under normal phase and polar organic separation modes. Influence of stationary and mobile phase type on resolution and elution order of enantiomers was studied. Results showed that the polysaccharide backbone of the stationary phase (amylose and cellulose) has a significant impact on chiral recognition, and the best separation was observed on amylose-based chiral stationary phases. It was established that steric effects play an important role on 4C-substituted pyrrolidin-2-one derivative resolution on polysaccharide-based chiral columns. Nature of alcohol in the mobile phase was also an important factor contributing not only to retention but also resolution. Although the use of the normal phase mode seems more beneficial, in certain cases, polar organic mode may increase the number of separated pairs of enantiomers.

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Authors and Affiliations

  1. Latvian Institute of Organic Synthesis, 21 Aizkraukles Street, Riga, 1006, Latvia

    Toms Upmanis, Helena Kažoka, Natalja Orlova & Maksims Vorona

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  1. Toms Upmanis
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  2. Helena Kažoka
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  3. Natalja Orlova
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  4. Maksims Vorona
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Correspondence to Helena Kažoka.

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Upmanis, T., Kažoka, H., Orlova, N. et al. Separation of 4C-Substituted Pyrrolidin-2-One Derivatives on Polysaccharide-Based Coated Chiral Stationary Phases. Chromatographia 83, 331–340 (2020). https://doi.org/10.1007/s10337-020-03862-7

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  • DOI: https://doi.org/10.1007/s10337-020-03862-7

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