ArticleNature communications2021
Organocatalytic enantioselective dearomatization of thiophenes by 1,10-conjugate addition of indole imine methides.
Article in Nature communications, 2021. 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
- Strategies for Enantioselective, Cascade, Valorizing, and Expanded Heterocyclic Piancatelli Rearrangements.ACS organic & inorganic Au · 2026Review
- Catalytic, Enantioselective Cycloaddition of Pyrrole-2Organic letters · 2024Article
- Combining photoredox catalysis and hydrogen atom transfer for dearomative functionalization of electron rich heteroarenes.Chemical science · 2023Article
- Chiral CoInorganic chemistry · 2023Article
- Large-Area Ordered Palladium Nanostructures by Colloidal Lithography for Hydrogen Sensing.Molecules (Basel, Switzerland) · 2022Article
- Organocatalytic discrimination of non-directing aryl and heteroaryl groups: enantioselective synthesis of bioactive indole-containing triarylmethanes.Chemical science · 2022Article
- Confronting the Challenging Asymmetric Carbonyl 1,2-Addition Using Vinyl Heteroarene Pronucleophiles: Ligand-Controlled Regiodivergent Processes through a Dearomatized Allyl-Cu Species.Journal of the American Chemical Society · 2022Article
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Authors and funding
5 authors.
Funding
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Abstract
Catalytic asymmetric dearomatization (CADA) is a powerful tool for the rapid construction of diverse chiral cyclic molecules from cheap and easily available arenes. This work reports an organocatalytic enantioselective dearomatization of substituted thiophenes in the context of a rare remote asymmetric 1,10-conjugate addition. By suitable stabilization of the thiophenyl carbocation with an indole motif in the form of indole imine methide, excellent remote chemo-, regio-, and stereocontrol in the nucleophilic addition can be achieved with chiral phosphoric acid catalysis under mild conditions. This protocol can be successfully extended to the asymmetric dearomatization of other heteroarenes including selenophenes and furans. Control experiments and DFT calculations demonstrate a possible pathway in which hydrogen bonding plays an important role in selectivity control.
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Registered trials
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