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

Ling-Feng Jiang, Shao-Hua Wu, Yu-Xuan Jiang, Hong-Xiang Ma, Jia-Jun He, Yang-Bo Bi, Kong De-Yi, Yi-Fei Cheng, Xuan Cheng and Qing-Hai Deng ()
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Ling-Feng Jiang: Shanghai Normal University
Shao-Hua Wu: Shanghai Normal University
Yu-Xuan Jiang: Shanghai Normal University
Hong-Xiang Ma: Shanghai Normal University
Jia-Jun He: Shanghai Normal University
Yang-Bo Bi: Shanghai Normal University
Kong De-Yi: Shanghai Normal University
Yi-Fei Cheng: Shanghai Normal University
Xuan Cheng: Shanghai Normal University
Qing-Hai Deng: Shanghai Normal University

Nature Communications, 2024, vol. 15, issue 1, 1-8

Abstract: 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.

Date: 2024
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DOI: 10.1038/s41467-024-49313-x

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