ArticleJournal of the American Chemical Society2022
Hypoiodite-Catalyzed Oxidative Umpolung of Indoles for Enantioselective Dearomatization.
Article in Journal of the American Chemical Society, 2022. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 8 papers.
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Who cites it
8 citing papers in PubMed.
- Catalytic Asymmetric Dearomative Cyclizations of Indolyldimethanols via Umpolung Strategy.JACS Au · 2026Article
- Divergent and Enantioselective Synthesis of Three Types of Chiral Polycyclic N‑Heterocycles via Copper-Catalyzed Dearomative Cyclization.ACS central science · 2025Article
- Asymmetric phase-transfer catalysis.Nature reviews. Chemistry · 2024Review
- Visible-Light-Induced Dearomative Annulation of Indoles toward Stereoselective Formation of Fused- and Spiro Indolines.ACS omega · 2024Review
- Switchable divergent synthesis of chiral indole derivativesRSC advances · 2024Article
- Mechanistic duality of indolyl 1,3-heteroatom transposition.Chemical science · 2023Article
- Copper-catalyzed oxidative dehydrogenative dearomatization of indole derivatives: A new strategy to construct spirocyclic indolenines.iScience · 2022Article
- Review
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4 authors.
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Abstract
Here we report the oxidative umpolung of 2,3-disubstituted indoles toward enantioselective dearomative aza-spirocyclization to give the corresponding spiroindolenines using chiral quaternary ammonium hypoiodite catalysis. Mechanistic studies revealed the umpolung reactivity of C3 of indoles by iodination of the indole nitrogen atom. Moreover, the introduction of pyrazole as an electron-withdrawing auxiliary group at C2 suppressed a competitive dissociative racemic pathway, and enantioselective spirocyclization proceeded to give not only spiropyrrolidines but also four-membered spiroazetidines that are otherwise difficult to access.
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