Enantioselective copper-catalyzed azidation/click cascade reaction for access to chiral 1,2,3-triazoles

Autor: Ling-Feng Jiang, Shao-Hua Wu, Yu-Xuan Jiang, Hong-Xiang Ma, Jia-Jun He, Yang-Bo Bi, De-Yi Kong, Yi-Fei Cheng, Xuan Cheng, Qing-Hai Deng
Jazyk: angličtina
Rok vydání: 2024
Předmět:
Zdroj: Nature Communications, Vol 15, Iss 1, Pp 1-8 (2024)
Druh dokumentu: article
ISSN: 2041-1723
DOI: 10.1038/s41467-024-49313-x
Popis: Abstract Chiral 1,2,3-triazoles are highly attractive motifs in various fields. However, achieving catalytic asymmetric click reactions of azides and alkynes for chiral triazole synthesis remains a significant challenge, mainly due to the limited catalytic systems and substrate scope. Herein, we report an enantioselective azidation/click cascade reaction of N-propargyl-β-ketoamides with a readily available and potent azido transfer reagent via copper catalysis, which affords a variety of chiral 1,2,3-triazoles with up to 99% yield and 95% ee under mild conditions. Notably, chiral 1,5-disubstituted triazoles that have not been accessed by previous asymmetric click reactions are also prepared with good functional group tolerance.
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