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Valence-isomer selective cycloaddition reaction of cycloheptatrienes-norcaradienes

Author

Listed:
  • Shingo Harada

    (Chiba University)

  • Hiroki Takenaka

    (Chiba University)

  • Tsubasa Ito

    (Chiba University)

  • Haruki Kanda

    (Chiba University)

  • Tetsuhiro Nemoto

    (Chiba University)

Abstract

The rapid and precise creation of complex molecules while controlling multiple selectivities is the principal objective in synthetic chemistry. Combining data science and organic synthesis to achieve this goal is an emerging trend, but few examples of successful reaction designs are reported. We develop an artificial neural network regression model using bond orbital data to predict chemical reactivities. Actual experimental verification confirms cycloheptatriene-selective [6 + 2]-cycloaddition utilizing nitroso compounds and norcaradiene-selective [4 + 2]-cycloaddition reactions employing benzynes. Additionally, a one-pot asymmetric synthesis is achieved by telescoping the enantioselective dearomatization of non-activated benzenes and cycloadditions. Computational studies provide a rational explanation for the seemingly anomalous occurrence of thermally prohibited suprafacial [6 + 2]-cycloaddition without photoirradiation.

Suggested Citation

  • Shingo Harada & Hiroki Takenaka & Tsubasa Ito & Haruki Kanda & Tetsuhiro Nemoto, 2024. "Valence-isomer selective cycloaddition reaction of cycloheptatrienes-norcaradienes," Nature Communications, Nature, vol. 15(1), pages 1-10, December.
    • Handle: RePEc:nat:natcom:v:15:y:2024:i:1:d:10.1038_s41467-024-46523-1
    DOI: 10.1038/s41467-024-46523-1
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    References listed on IDEAS

    as
    1. Hak Joong Kim & Mark W. Ruszczycky & Sei-hyun Choi & Yung-nan Liu & Hung-wen Liu, 2011. "Enzyme-catalysed [4+2] cycloaddition is a key step in the biosynthesis of spinosyn A," Nature, Nature, vol. 473(7345), pages 109-112, May.
    2. Marwin H. S. Segler & Mike Preuss & Mark P. Waller, 2018. "Planning chemical syntheses with deep neural networks and symbolic AI," Nature, Nature, vol. 555(7698), pages 604-610, March.
    3. Jolene P. Reid & Matthew S. Sigman, 2019. "Holistic prediction of enantioselectivity in asymmetric catalysis," Nature, Nature, vol. 571(7765), pages 343-348, July.
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