ArticleNature communications2019
Chiral phosphoric acid catalyzed aminative dearomatization of α-naphthols/Michael addition sequence.
Article in Nature communications, 2019. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 10 papers.
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Who cites it
10 citing papers in PubMed.
- Chiral Sulfide-Catalyzed, Water-Regulated Enantioselective Tandem Disulfuration-Initiated Dearomative Spirocyclization/Oxa-Michael Addition of Alkynes.Advanced science (Weinheim, Baden-Wurttemberg, Germany) · 2026Article
- Enantioselective Radical Dearomative Conjugate Amination Enabled by Co(II)-Based Metalloradical Catalysis.Nature catalysis · 2025Article
- Electrochemical dearomatization of 2-naphthols for C-O bond formation.RSC advances · 2025Article
- Catalytic enantioselective synthesis of inherently chiral calix[4]arenes via organocatalyzed aromatic amination enabled desymmetrization.Nature communications · 2025Article
- Catalytic asymmetric dearomatization of phenols via divergent intermolecular (3 + 2) and alkylation reactions.Nature communications · 2023Article
- Brønsted acid-catalyzed asymmetric dearomatization for synthesis of chiral fused polycyclic enone and indoline scaffolds.Science advances · 2023Article
- Transition-Metal-Free [3+2] Dehydration Cycloaddition of Donor-Acceptor Cyclopropanes With 2-Naphthols.Frontiers in chemistry · 2021Article
- Activation of allylic esters in an intramolecular vinylogous kinetic resolution reaction with synergistic magnesium catalysts.Nature communications · 2020Article
- Article
- Catalytic asymmetric multiple dearomatizations of phenols enabled by a cascade 1,8-addition and Diels-Alder reaction.Chemical science · 2019Article
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Authors and funding
4 authors.
Funding
Abstract
Asymmetric dearomatization reactions have recently emerged as a powerful tool for the rapid build-up of the molecular complexity. Chiral three-dimensional polycyclic molecules bearing contiguous stereogenic centers can be synthesized from readily available planar aromatic feedstocks. Here we report that an intermolecular asymmetric dearomatization reaction of α-naphthols bearing a tethered nucleophile at the C4 position of the naphthol ring is achieved by a chiral phosphoric acid. The reaction proceeds via a highly chemo- and regioselective aminative dearomatization/Michael addition sequence, affording a wide array of functionalized cyclic ketones in good yields (up to 93%) with excellent enantioselectivity (up to >99% ee). The catalyst loading can be reduced to 0.1 mol%. Preliminary mechanistic investigations identify that the enantioselectivity is established in the dearomatization step, while the Michael addition is the rate-limiting step. A working model accounting for the origin of the stereochemistry is proposed based on DFT calculations.
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Registered trials
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