Enantioselective copper-catalyzed azidation/click cascade reaction for access to chiral 1,2,3-triazoles.
basic_science · Level V
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- Record sourced from PubMed, PMID 38858346.
- Also identified by DOI 10.1038/s41467-024-49313-x and PMC identifier 11164697.
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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.