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Conformational enantiodiscrimination for asymmetric construction of atropisomers

Author

Listed:
  • Shouyi Cen

    (East China University of Science & Technology)

  • Nini Huang

    (East China University of Science & Technology)

  • Dongsheng Lian

    (East China University of Science & Technology)

  • Ahui Shen

    (East China University of Science & Technology)

  • Mei-Xin Zhao

    (East China University of Science & Technology)

  • Zhipeng Zhang

    (East China University of Science & Technology)

Abstract

Molecular conformations induced by the rotation about single bonds play a crucial role in chemical transformations. Revealing the relationship between the conformations of chiral catalysts and the enantiodiscrimination is a formidable challenge due to the great difficulty in isolating the conformers. Herein, we report a chiral catalytic system composed of an achiral catalytically active unit and an axially chiral 1,1′-bi-2-naphthol (BINOL) unit which are connected via a C–O single bond. The two conformers of the catalyst induced by the rotation about the C–O bond, are determined via single-crystal X-ray diffraction and found to respectively lead to the formation of highly important axially chiral 1,1′-binaphthyl-2,2′-diamine (BINAM) and 2-amino-2′-hydroxy-1,1′-binaphthyl (NOBIN) derivatives in high yields (up to 98%), with excellent enantioselectivities (up to 98:2 e.r.) and opposite absolute configurations. The results highlight the importance of conformational dynamics of chiral catalysts in asymmetric catalysis.

Suggested Citation

  • Shouyi Cen & Nini Huang & Dongsheng Lian & Ahui Shen & Mei-Xin Zhao & Zhipeng Zhang, 2022. "Conformational enantiodiscrimination for asymmetric construction of atropisomers," Nature Communications, Nature, vol. 13(1), pages 1-7, December.
    • Handle: RePEc:nat:natcom:v:13:y:2022:i:1:d:10.1038_s41467-022-32432-8
    DOI: 10.1038/s41467-022-32432-8
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    References listed on IDEAS

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    1. Gongming Yang & Donghui Guo & Di Meng & Jian Wang, 2019. "NHC-catalyzed atropoenantioselective synthesis of axially chiral biaryl amino alcohols via a cooperative strategy," Nature Communications, Nature, vol. 10(1), pages 1-6, December.
    2. Shenci Lu & Shawn Voon Hwee Ng & Kaitlyn Lovato & Jun-Yang Ong & Si Bei Poh & Xiao Qian Ng & László Kürti & Yu Zhao, 2019. "Practical access to axially chiral sulfonamides and biaryl amino phenols via organocatalytic atroposelective N-alkylation," Nature Communications, Nature, vol. 10(1), pages 1-10, December.
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