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Synthesis of Cross-Chain Bridging Cryptands and Induction of Molecular Chirality

  • Hiroki Fujihara
    Hiroki Fujihara
    Department of Materials Science and Engineering, Faculty of Engineering, University of Fukui, Bunkyo, Fukui 910-8507, Japan
  • Masaya Naito
    Masaya Naito
    Department of Materials Science and Engineering, Faculty of Engineering, University of Fukui, Bunkyo, Fukui 910-8507, Japan
    More by Masaya Naito
  • Takafumi Yashima
    Takafumi Yashima
    Department of Materials Science and Engineering, Faculty of Engineering, University of Fukui, Bunkyo, Fukui 910-8507, Japan
  • Yusuke Okada
    Yusuke Okada
    Faculty of Textile Science and Technology, Shinshu University, Tokida, Ueda, Nagano 386-8567, Japan
    More by Yusuke Okada
  • Nagao Kobayashi
    Nagao Kobayashi
    Faculty of Textile Science and Technology, Shinshu University, Tokida, Ueda, Nagano 386-8567, Japan
  • Shinobu Miyagawa
    Shinobu Miyagawa
    Department of Materials Science and Engineering, Faculty of Engineering, University of Fukui, Bunkyo, Fukui 910-8507, Japan
  • Hikaru Takaya
    Hikaru Takaya
    Department of Life Science, Faculty of Life & Environmental Sciences, Teikyo University of Science, Main Buld #15-05, 2-2-1 Senjyusakuragi, Adachi-ku, Tokyo 120-0045, Japan
    Division of Photo-Molecular Science, Institute for Molecular Science, Myodaiji, Okazaki, Aichi 444-8585, Japan
  • , and 
  • Yuji Tokunaga*
    Yuji Tokunaga
    Department of Materials Science and Engineering, Faculty of Engineering, University of Fukui, Bunkyo, Fukui 910-8507, Japan
    *Email: [email protected]
Cite this: Org. Lett. 2023, 25, 50, 8959–8964
Publication Date (Web):October 23, 2023
https://doi.org/10.1021/acs.orglett.3c03007
Copyright © 2023 American Chemical Society

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    Abstract

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    In this study, we synthesized two cryptands featuring entangled tri- and tetra(ethylene glycol) linkers. The cryptand bearing short linkers was chiral without any asymmetric carbon atoms. After chiral high-performance liquid chromatography was used to separate the enantiomers, the absolute configuration of each cryptand was determined through single-crystal X-ray and circular dichroism analyses. The racemization of the cryptand possessing long linkers proceeded at room temperature.

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    The Supporting Information is available free of charge at https://pubs.acs.org/doi/10.1021/acs.orglett.3c03007.

    • Full experimental procedures, compound characterization, X-ray crystallographic data, and computational details (PDF)

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    CCDC 2267806 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge via www.ccdc.cam.ac.uk/data_request/cif, or by emailing [email protected], or by contacting The Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB2 1EZ, UK; fax: + 44 1223 336033.

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