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Photocatalytic Z/E isomerization unlocking the stereodivergent construction of axially chiral alkene frameworks

Author

Listed:
  • Jie Wang

    (Nanjing University of Science and Technology)

  • Jun Gu

    (Nanjing University of Science and Technology)

  • Jia-Yu Zou

    (Nanjing University of Science and Technology)

  • Meng-Jie Zhang

    (Nanjing University of Science and Technology)

  • Rui Shen

    (Nanjing University of Science and Technology)

  • Zhiwen Ye

    (Nanjing University of Science and Technology)

  • Ping-Xun Xu

    (Nanjing University of Science and Technology)

  • Ying He

    (Nanjing University of Science and Technology)

Abstract

The past century has witnessed a large number of reports on the Z/E isomerization of alkenes. However, the vast majority of them are still limited to the isomerization of di- and tri-substituted alkenes. The stereospecific Z/E isomerization of tetrasubstituted alkenes remains to be an underdeveloped area, thus lacking in a stereodivergent synthesis of axially chiral alkenes. Herein we report the atroposelective synthesis of tetrasubstituted alkene analogues by asymmetric allylic substitution-isomerization, followed by their Z/E isomerization via triplet energy transfer photocatalysis. In this regard, the stereodivergent synthesis of axially chiral N-vinylquinolinones is achieved efficiently. Mechanistic studies indicate that the benzylic radical generation and distribution are two key factors for preserving the enantioselectivities of axially chiral compounds.

Suggested Citation

  • Jie Wang & Jun Gu & Jia-Yu Zou & Meng-Jie Zhang & Rui Shen & Zhiwen Ye & Ping-Xun Xu & Ying He, 2024. "Photocatalytic Z/E isomerization unlocking the stereodivergent construction of axially chiral alkene frameworks," Nature Communications, Nature, vol. 15(1), pages 1-8, December.
    • Handle: RePEc:nat:natcom:v:15:y:2024:i:1:d:10.1038_s41467-024-47404-3
    DOI: 10.1038/s41467-024-47404-3
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    References listed on IDEAS

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    1. Tibor Kudernac & Nopporn Ruangsupapichat & Manfred Parschau & Beatriz Maciá & Nathalie Katsonis & Syuzanna R. Harutyunyan & Karl-Heinz Ernst & Ben L. Feringa, 2011. "Electrically driven directional motion of a four-wheeled molecule on a metal surface," Nature, Nature, vol. 479(7372), pages 208-211, November.
    2. Thach T. Nguyen & Ming Joo Koh & Tyler J. Mann & Richard R. Schrock & Amir H. Hoveyda, 2017. "Synthesis of E- and Z-trisubstituted alkenes by catalytic cross-metathesis," Nature, Nature, vol. 552(7685), pages 347-354, December.
    3. Sheng-Cai Zheng & San Wu & Qinghai Zhou & Lung Wa Chung & Liu Ye & Bin Tan, 2017. "Erratum: Organocatalytic atroposelective synthesis of axially chiral styrenes," Nature Communications, Nature, vol. 8(1), pages 1-1, December.
    4. Nagatoshi Koumura & Robert W. J. Zijlstra & Richard A. van Delden & Nobuyuki Harada & Ben L. Feringa, 1999. "Light-driven monodirectional molecular rotor," Nature, Nature, vol. 401(6749), pages 152-155, September.
    5. Sheng-Cai Zheng & San Wu & Qinghai Zhou & Lung Wa Chung & Liu Ye & Bin Tan, 2017. "Organocatalytic atroposelective synthesis of axially chiral styrenes," Nature Communications, Nature, vol. 8(1), pages 1-9, August.
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