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Site-switchable mono-O-allylation of polyols

Author

Listed:
  • Hua Tang

    (Sichuan University)

  • Yu-Biao Tian

    (Sichuan University)

  • Hongyan Cui

    (Sichuan University)

  • Ren-Zhe Li

    (Sichuan University)

  • Xia Zhang

    (Sichuan University)

  • Dawen Niu

    (Sichuan University
    China Pharmaceutical University)

Abstract

Site-selective modification of complex molecules allows for rapid accesses to their analogues and derivatives, and, therefore, offers highly valuable opportunities to probe their functions. However, to selectively manipulate one out of many repeatedly occurring functional groups within a substrate represents a grand challenge in chemistry. Yet more demanding is to develop methods in which alterations to the reaction conditions lead to switching of the specific site of reaction. We report herein the development of a Pd/Lewis acid co-catalytic system that achieves not only site-selective, but site-switchable mono-O-allylation of polyols with readily available reagents and catalysts. Through exchanging the Lewis acid additives that recognize specific hydroxyls in a polyol substrate, our system managed to install a versatile allyl group to the target in a site-switchable manner. Our design demonstrates remarkable scope, and is amenable to the direct derivatization of various complex, bioactive natural products.

Suggested Citation

  • Hua Tang & Yu-Biao Tian & Hongyan Cui & Ren-Zhe Li & Xia Zhang & Dawen Niu, 2020. "Site-switchable mono-O-allylation of polyols," Nature Communications, Nature, vol. 11(1), pages 1-10, December.
    • Handle: RePEc:nat:natcom:v:11:y:2020:i:1:d:10.1038_s41467-020-19348-x
    DOI: 10.1038/s41467-020-19348-x
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