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Asymmetric synthesis using chiral-encoded metal

Author

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  • Thittaya Yutthalekha

    (Univ. Bordeaux, CNRS UMR 5255, Bordeaux INP, ENSCBP
    Faculty of Science, Kasetsart University
    NANOTEC Center for Nanoscale Materials Design for Green Nanotechnology, Faculty of Science, Kasetsart University
    School of Energy Science and Engineering, Vidyasirimedhi Institute of Science and Technology)

  • Chularat Wattanakit

    (School of Energy Science and Engineering, Vidyasirimedhi Institute of Science and Technology)

  • Veronique Lapeyre

    (Univ. Bordeaux, CNRS UMR 5255, Bordeaux INP, ENSCBP)

  • Somkiat Nokbin

    (Faculty of Science, Kasetsart University
    NANOTEC Center for Nanoscale Materials Design for Green Nanotechnology, Faculty of Science, Kasetsart University)

  • Chompunuch Warakulwit

    (Faculty of Science, Kasetsart University
    NANOTEC Center for Nanoscale Materials Design for Green Nanotechnology, Faculty of Science, Kasetsart University)

  • Jumras Limtrakul

    (School of Molecular Science and Engineering, Vidyasirimedhi Institute of Science and Technology)

  • Alexander Kuhn

    (Univ. Bordeaux, CNRS UMR 5255, Bordeaux INP, ENSCBP)

Abstract

The synthesis of chiral compounds is of crucial importance in many areas of society and science, including medicine, biology, chemistry, biotechnology and agriculture. Thus, there is a fundamental interest in developing new approaches for the selective production of enantiomers. Here we report the use of mesoporous metal structures with encoded geometric chiral information for inducing asymmetry in the electrochemical synthesis of mandelic acid as a model molecule. The chiral-encoded mesoporous metal, obtained by the electrochemical reduction of platinum salts in the presence of a liquid crystal phase and the chiral template molecule, perfectly retains the chiral information after removal of the template. Starting from a prochiral compound we demonstrate enantiomeric excess of the (R)-enantiomer when using (R)-imprinted electrodes and vice versa for the (S)-imprinted ones. Moreover, changing the amount of chiral cavities in the material allows tuning the enantioselectivity.

Suggested Citation

  • Thittaya Yutthalekha & Chularat Wattanakit & Veronique Lapeyre & Somkiat Nokbin & Chompunuch Warakulwit & Jumras Limtrakul & Alexander Kuhn, 2016. "Asymmetric synthesis using chiral-encoded metal," Nature Communications, Nature, vol. 7(1), pages 1-8, November.
    • Handle: RePEc:nat:natcom:v:7:y:2016:i:1:d:10.1038_ncomms12678
    DOI: 10.1038/ncomms12678
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    Cited by:

    1. Si Li & Xinxin Xu & Liguang Xu & Hengwei Lin & Hua Kuang & Chuanlai Xu, 2024. "Emerging trends in chiral inorganic nanomaterials for enantioselective catalysis," Nature Communications, Nature, vol. 15(1), pages 1-8, December.
    2. Maryam Arabi & Abbas Ostovan & Yunqing Wang & Rongchao Mei & Longwen Fu & Jinhua Li & Xiaoyan Wang & Lingxin Chen, 2022. "Chiral molecular imprinting-based SERS detection strategy for absolute enantiomeric discrimination," Nature Communications, Nature, vol. 13(1), pages 1-14, December.

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