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- Title
Enantioselective copper-catalyzed azidation/click cascade reaction for access to chiral 1,2,3-triazoles.
- Authors
Jiang, Ling-Feng; Wu, Shao-Hua; Jiang, Yu-Xuan; Ma, Hong-Xiang; He, Jia-Jun; Bi, Yang-Bo; Kong, De-Yi; Cheng, Yi-Fei; Cheng, Xuan; Deng, Qing-Hai
- 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. Catalytic asymmetric click reactions of azides and alkynes for chiral triazole synthesis remains a challenge, due to the limited catalytic systems and substrate scope. Herein, the authors report the enantioselective azidation/click cascade reaction of N-propargyl-β-ketoamides via copper catalysis, affording a variety of chiral 1,2,3-triazoles.
- Subjects
AZIDATION; COPPER; BIOCHEMICAL substrates; AZIDES; FUNCTIONAL groups
- Publication
Nature Communications, 2024, Vol 15, Issue 1, p1
- ISSN
2041-1723
- Publication type
Article
- DOI
10.1038/s41467-024-49313-x