Chemoselective Amide‐Forming Ligation Between Acylsilanes and Hydroxylamines Under Aqueous Conditions

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Abstract
We report the facile amide‐forming ligation of acylsilanes with hydroxylamines (ASHA ligation) under aqueous conditions. The ligation is fast, chemoselective, mild, high‐yielding and displays excellent functional‐group tolerance. Late‐stage modifications of an array of marketed drugs, peptides, natural products, and biologically active compounds showcase the robustness and functional‐group tolerance of the reaction. The key to the success of the reaction could be the possible formation of the strong Si−O bond via a Brook‐type rearrangement. Given its simplicity and efficiency, this ligation has the potential to unfold new applications in the areas of medicinal chemistry and chemical biology.
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  • Tianjin University

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