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Stereodivergent 1,3-difunctionalization of alkenes by charge relocation

Author

Listed:
  • Bogdan R. Brutiu

    (University of Vienna)

  • Giulia Iannelli

    (University of Vienna)

  • Margaux Riomet

    (University of Vienna)

  • Daniel Kaiser

    (University of Vienna)

  • Nuno Maulide

    (University of Vienna
    Research Platform NeGeMac)

Abstract

Alkenes are indispensable feedstocks in chemistry. Functionalization at both carbons of the alkene—1,2-difunctionalization—is part of chemistry curricula worldwide1. Although difunctionalization at distal positions has been reported2–4, it typically relies on designer substrates featuring directing groups and/or stabilizing features, all of which determine the ultimate site of bond formation5–7. Here we introduce a method for the direct 1,3-difunctionalization of alkenes, based on a concept termed ‘charge relocation’, which enables stereodivergent access to 1,3-difunctionalized products of either syn- or anti-configuration from unactivated alkenes, without the need for directing groups or stabilizing features. The usefulness of the approach is demonstrated in the synthesis of the pulmonary toxin 4-ipomeanol and its derivatives.

Suggested Citation

  • Bogdan R. Brutiu & Giulia Iannelli & Margaux Riomet & Daniel Kaiser & Nuno Maulide, 2024. "Stereodivergent 1,3-difunctionalization of alkenes by charge relocation," Nature, Nature, vol. 626(7997), pages 92-97, February.
    • Handle: RePEc:nat:nature:v:626:y:2024:i:7997:d:10.1038_s41586-023-06938-0
    DOI: 10.1038/s41586-023-06938-0
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