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Asymmetric 1,4-functionalization of 1,3-enynes via dual photoredox and chromium catalysis

Author

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  • Feng-Hua Zhang

    (Westlake University
    Westlake Institute for Advanced Study)

  • Xiaochong Guo

    (Westlake University
    Westlake Institute for Advanced Study)

  • Xianrong Zeng

    (Westlake University
    Westlake Institute for Advanced Study)

  • Zhaobin Wang

    (Westlake University
    Westlake Institute for Advanced Study)

Abstract

The merger of photoredox and transition-metal catalysis has evolved as a robust platform in organic synthesis over the past decade. The stereoselective 1,4-functionalization of 1,3-enynes, a prevalent synthon in synthetic chemistry, could afford valuable chiral allene derivatives. However, tremendous efforts have been focused on the ionic reaction pathway. The radical-involved asymmetric 1,4-functionalization of 1,3-enynes remains a prominent challenge. Herein, we describe the asymmetric three-component 1,4-dialkylation of 1,3-enynes via dual photoredox and chromium catalysis to provide chiral allenols. This method features readily available starting materials, broad substrate scope, good functional group compatibility, high regioselectivity, and simultaneous control of axial and central chiralities. Mechanistic studies suggest that this reaction proceeds through a radical-involved redox-neutral pathway.

Suggested Citation

  • Feng-Hua Zhang & Xiaochong Guo & Xianrong Zeng & Zhaobin Wang, 2022. "Asymmetric 1,4-functionalization of 1,3-enynes via dual photoredox and chromium catalysis," Nature Communications, Nature, vol. 13(1), pages 1-11, December.
    • Handle: RePEc:nat:natcom:v:13:y:2022:i:1:d:10.1038_s41467-022-32614-4
    DOI: 10.1038/s41467-022-32614-4
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