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Anionic Bisoxazoline Ligands Enable Copper‐Catalyzed Asymmetric Radical Azidation of Acrylamides
Author(s) -
Wu Lianqian,
Zhang Zhihan,
Wu Dunqi,
Wang Fei,
Chen Pinhong,
Lin Zhenyang,
Liu Guosheng
Publication year - 2021
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.202015083
Subject(s) - enantioselective synthesis , azide , chemistry , catalysis , monomer , copper , ligand (biochemistry) , yield (engineering) , combinatorial chemistry , polymer chemistry , organic chemistry , polymer , materials science , receptor , biochemistry , metallurgy
Asymmetric radical azidation for the synthesis of chiral alkylazides remains a tremendous challenge in organic synthesis. We report here an unprecedented highly enantioselective radical azidation of acrylamides catalyzed by 1 mol % of a copper catalyst. The substrates were converted to the corresponding alkylazides in high yield with good‐to‐excellent enantioselectivity. Notably, employing an anionic cyano‐bisoxazoline (CN‐Box) ligand is crucial to generate a monomeric Cu II azide species, rather than a dimeric Cu II azide intermediate, for this highly enantioselective radical azidation.