Synthesis of Cyclopenta[b]indoles via Rhodium‐Catalyzed Cascade Migration‐Annulation of 1‐Sulfonyl‐1,2,3‐triazoles and Indoles

A rhodium‐catalyzed cascade 1,3‐sulfinate migration, intermolecular [3+2] annulation of 1‐sulfonyl‐1,2,3‐triazoles and indoles was achieved. The one‐pot protocol provided a method to construct cyclopenta[b]indoles bearing four stereocenters in 45% to 99% yields with 1.6:1 to >20:1 diastereoselect...

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Veröffentlicht in:Advanced synthesis & catalysis 2023-05, Vol.365 (10), p.1623-1628
Hauptverfasser: Xu, Huaping, Wang, Heng, Xu, Ze‐Feng, Duan, Shengguo, Li, Chuan‐Ying
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Sprache:eng
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Zusammenfassung:A rhodium‐catalyzed cascade 1,3‐sulfinate migration, intermolecular [3+2] annulation of 1‐sulfonyl‐1,2,3‐triazoles and indoles was achieved. The one‐pot protocol provided a method to construct cyclopenta[b]indoles bearing four stereocenters in 45% to 99% yields with 1.6:1 to >20:1 diastereoselectivities. In addition, cyclopenta[b]indoles could be transformed into a variety of functionalized compounds, demonstrating the synthetic value of this migration‐annulation strategy in ring system synthesis.
ISSN:1615-4150
1615-4169
DOI:10.1002/adsc.202300241