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Regioselective activation of benzocyclobutenones and dienamides lead to anti-Bredt bridged-ring systems by a [4+4] cycloaddition

Author

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  • Jianyu Zhang

    (Ocean University of China)

  • Xi Wang

    (Ocean University of China)

  • Tao Xu

    (Ocean University of China
    Pilot National Laboratory for Marine Science and Technology)

Abstract

To the best of our knowledge, bridgehead carbon benzofused-bridged ring systems have previously not been accessible to the synthetic community. Here, we describe a formal type-II [4 + 4] cycloaddition approach that provides fully sp2-carbon embedded anti-Bredt bicyclo[5.3.1] skeletons through the Rh-catalyzed C1–C8 activation of benzocyclobutenones (BCBs) and their coupling with pedant dienamides. Variously substituted dienamides have been coupled with BCBs to provide a range of complex bicyclo[5.3.1] scaffolds (>20 examples, up to 89% yield). The bridged rings were further converted to polyfused hydroquinoline-containing tetracycles via a serendipitously discovered transannular 1,5-hydride shift/Prins-like cyclization/Schmidt rearrangement cascade.

Suggested Citation

  • Jianyu Zhang & Xi Wang & Tao Xu, 2021. "Regioselective activation of benzocyclobutenones and dienamides lead to anti-Bredt bridged-ring systems by a [4+4] cycloaddition," Nature Communications, Nature, vol. 12(1), pages 1-8, December.
    • Handle: RePEc:nat:natcom:v:12:y:2021:i:1:d:10.1038_s41467-021-23344-0
    DOI: 10.1038/s41467-021-23344-0
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    Cited by:

    1. Kemiao Hong & Mengting Liu & Lixin Qian & Ming Bao & Gang Chen & Xinyu Jiang & Jingjing Huang & Xinfang Xu, 2024. "Catalytic [4+2]- and [4+4]-cycloaddition using furan-fused cyclobutanone as a privileged C4 synthon," Nature Communications, Nature, vol. 15(1), pages 1-11, December.

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