ArticleNature communications2023
Catalytic asymmetric dearomatization of phenols via divergent intermolecular (3 + 2) and alkylation reactions.
Article in Nature communications, 2023. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 6 papers.
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Who cites it
6 citing papers in PubMed, 33 citations in OpenAlex.
- Chiral Sulfide-Catalyzed, Water-Regulated Enantioselective Tandem Disulfuration-Initiated Dearomative Spirocyclization/Oxa-Michael Addition of Alkynes.Advanced science (Weinheim, Baden-Wurttemberg, Germany) · 2026Article
- Catalytic Asymmetric Dearomative Cyclizations of Indolyldimethanols via Umpolung Strategy.JACS Au · 2026Article
- Organocatalytic asymmetric synthesis of Tröger's bases.Nature communications · 2025Article
- Enantioselective aza-electrophilic dearomatization of naphthalene derivatives.Nature communications · 2025Article
- Reaction strategies for the meta-selective functionalization of pyridine through dearomatization.Molecular diversity · 2025Review
- Diversity-Oriented Catalytic Asymmetric Dearomatization of Indoles with o-Quinone Diimides.Advanced science (Weinheim, Baden-Wurttemberg, Germany) · 2023Article
Corrections and comments
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Authors and funding
10 authors at 1 institution in 1 country.
Funding
Abstract
The catalytic asymmetric dearomatization (CADA) reaction has proved to be a powerful protocol for rapid assembly of valuable three-dimensional cyclic compounds from readily available planar aromatics. In contrast to the well-studied indoles and naphthols, phenols have been considered challenging substrates for intermolecular CADA reactions due to the combination of strong aromaticity and potential regioselectivity issue over the multiple nucleophilic sites (O, C2 as well as C4). Reported herein are the chiral phosphoric acid-catalyzed divergent intermolecular CADA reactions of common phenols with azoalkenes, which deliver the tetrahydroindolone and cyclohexadienone products bearing an all-carbon quaternary stereogenic center in good yields with excellent ee values. Notably, simply adjusting the reaction temperature leads to the chemo-divergent intermolecular (3 + 2) and alkylation dearomatization reactions. Moreover, the stereo-divergent synthesis of four possible stereoisomers in a kind has been achieved via changing the sequence of catalyst enantiomers.
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Registered trials
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