Separation-free Enantiodifferentiation with Chromatogram-like Output

Yipeng Li; Lixian Wen; Huan Meng; Jinghuang Lv; Gen Luo; Yanchuan Zhao

Cell Reports Physical Science (Jul 2020)

Separation-free Enantiodifferentiation with Chromatogram-like Output

Yipeng Li,
Lixian Wen,
Huan Meng,
Jinghuang Lv,
Gen Luo,
Yanchuan Zhao

Affiliations

Yipeng Li: Key Laboratory of Organofluorine Chemistry, Center for Excellence in Molecular Synthesis, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Beijing, China
Lixian Wen: Key Laboratory of Organofluorine Chemistry, Center for Excellence in Molecular Synthesis, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Beijing, China
Huan Meng: Key Laboratory of Organofluorine Chemistry, Center for Excellence in Molecular Synthesis, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Beijing, China
Jinghuang Lv: Key Laboratory of Organofluorine Chemistry, Center for Excellence in Molecular Synthesis, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Beijing, China
Gen Luo: Key Laboratory of Organofluorine Chemistry, Center for Excellence in Molecular Synthesis, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Beijing, China
Yanchuan Zhao: Key Laboratory of Organofluorine Chemistry, Center for Excellence in Molecular Synthesis, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Beijing, China; Key Laboratory of Energy Regulation Materials, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Beijing, China; Corresponding author

Journal volume & issue: Vol. 1, no. 7
p. 100100

Abstract

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Summary: Chromatographic-based approaches are most widely used for the analysis of enantiomers. Unambiguous results are achieved through the visualization of each enantiomer, while the separation process is often time consuming. By endowing 19F probes with suitable dynamic recognition properties, we develop here a detection scheme that produces chromatogram-like output in the analysis of enantiomeric mixtures without separation. A wide range of chiral compounds, including alcohols, ethers, amides, carbamates, oxazolidinones, sulfoxides, and sulfoximines, are successfully resolved, and the simultaneous enantiodifferentiation of different classes of chiral compounds is achieved. The method is also amenable for the determination of the enantiopurity of crude reaction products and the assignment of absolute configurations. The potential utility in high-throughput screening is demonstrated by the analysis of 24 nonracemic samples in 30 min with an NMR spectrometer equipped with an autosampler.

Published in Cell Reports Physical Science

ISSN: 2666-3864 (Online)
Publisher: Elsevier
Country of publisher: United States
LCC subjects: Science: Physics
Website: https://www.cell.com/cell-reports-physical-science

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