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Chemoselective Amide‐Forming Ligation Between Acylsilanes and Hydroxylamines Under Aqueous Conditions
Author(s) -
Deng Xingwang,
Zhou Guan,
Tian Jing,
Srinivasan Rajavel
Publication year - 2021
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.202012459
Subject(s) - ligation , amide , functional group , chemistry , combinatorial chemistry , aqueous solution , native chemical ligation , organic chemistry , chemical synthesis , biochemistry , in vitro , medicine , surgery , polymer
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.