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Analysis of Stereochemical Stability of Dynamic Chiral Molecules Using an Automated Microflow Measurement System

Cite this: J. Org. Chem. 2021, 86, 14, 9651–9657
Publication Date (Web):July 7, 2021
https://doi.org/10.1021/acs.joc.1c00914
Copyright © 2021 American Chemical Society

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    Abstract

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    An automated microflow measurement system for the kinetic study of racemization of dynamic chiral molecules was developed. This system facilitated the analysis of fast racemization within several seconds at elevated temperatures owing to its rapid heating ability, high performance for controlling short residence times, and ease of connection to HPLC systems for direct measurement of the enantiomeric purity. A more precise analysis was realized by combination of microflow and common batch measurements over a broad range of temperatures.

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    The Supporting Information is available free of charge at https://pubs.acs.org/doi/10.1021/acs.joc.1c00914.

    • Analytical data for stereochemical stability of DYCMs, synthetic scheme for compound 2a, and NMR spectra for newly reported compounds (PDF)

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    Cited By

    This article is cited by 4 publications.

    1. Shusaku Asano, Samuel J. Adams, Yuta Tsuji, Kazunari Yoshizawa, Atsushi Tahara, Jun-ichiro Hayashi, Nikolay Cherkasov. Homogeneous catalyst modifier for alkyne semi-hydrogenation: systematic screening in an automated flow reactor and computational study on mechanisms. Reaction Chemistry & Engineering 2022, 7 (8) , 1818-1826. https://doi.org/10.1039/D2RE00147K
    2. Kazunobu Igawa, Kazuhiro Uehara, Yuuya Kawasaki, Katsuhiko Tomooka. Stereochemical study on planar‐chiral cyclic molecules using polysaccharide‐based column chromatography. Chirality 2022, 34 (6) , 824-832. https://doi.org/10.1002/chir.23429
    3. Rosa López, Claudio Palomo. Planar Chirality: A Mine for Catalysis and Structure Discovery. Angewandte Chemie 2022, 134 (13) https://doi.org/10.1002/ange.202113504
    4. Rosa López, Claudio Palomo. Planar Chirality: A Mine for Catalysis and Structure Discovery. Angewandte Chemie International Edition 2022, 61 (13) https://doi.org/10.1002/anie.202113504

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