Journal
ORGANIC LETTERS
Volume 23, Issue 21, Pages 8365-8369Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.1c03106
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Funding
- National Natural Science Foundation of China [21871218]
- Natural Science Basic Research Plan in Shaanxi Province of China [2021JM-004]
- China Postdoctoral Science Foundation [2019M663660]
- Fundamental Research Funds for the Central Universities
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A rhodium-catalyzed diastereoselective formal [5 + 2] annulation of indoles with cyclohexadienone-containing 1,6-enynes has been successfully established via indole 2,3-difunctionalization. This method allows for rapid construction of indole-fused oxepines with a broad substrate scope and simultaneous formation of cis-hydrobenzo[b] oxepine scaffolds, which are core units found in natural products with important biological activities.
A rhodium-catalyzed diastereoselective formal [5 + 2] annulation of indoles with cyclohexadienone-containing 1,6-enynes has been established via indole 2,3-difunctionalization. The reaction, probably proceeding through tandem indole C2-H alkenylation and intramolecular Friedel-Crafts alkylation relay, provides rapid construction of indole-fused oxepines in good to excellent yields with a broad substrate scope. This method also features concomitant construction of cis-hydrobenzo[b] oxepine scaffolds, a core unit found in numerous natural products of important biological activities.
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