ArticleNature chemistry2021
Asymmetric, visible light-mediated radical sulfinyl-Smiles rearrangement to access all-carbon quaternary stereocentres.
Article in Nature chemistry, 2021. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 41 papers.
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41 citing papers in PubMed, 195 citations in OpenAlex.
- A radical-polar crossover approach to complex nitrogen heterocycles via the triplet state.Chem · 2026Article
- Remote 1,5-Difunctionalization of Alkenes via a Sulfinyl-Smiles Rearrangement and Vinylcyclopropane Ring-Opening Cascade.JACS Au · 2026Article
- Arene difunctionalization through an acyl-inserting Smiles rearrangement enabled by N-heterocyclic carbene catalysis.Nature communications · 2026Article
- Stereoselective Photoenzymatic Hydroarylation for the Construction of Quaternary Stereocenters.Journal of the American Chemical Society · 2025Article
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- Synthesis of Sterically Congested Carbonyl Compounds via anJournal of the American Chemical Society · 2025Article
- Smiles-Truce Cascades Enable Heteroaryl Cyclopropane and Sultine Synthesis.Angewandte Chemie (International ed. in English) · 2025Article
- Recent synthetic methodology advancements towards all-carbon quaternary center formation and applications.Tetrahedron · 2025Article
- Advancing Sulfinyl Radical Chemistry: An Asymmetric Smiles Rearrangement with Chiral Sulfoxides.Angewandte Chemie (International ed. in English) · 2025Article
- Amines tuned controllable carbonylation for the synthesis of γ-lactones and 1,4-diones.Nature communications · 2025Article
- Merging Hydrogen-Atom-Transfer and the Truce-Smiles Rearrangement for Synthesis of β-Arylethylamines from Unactivated Allylsulfonamides.Angewandte Chemie (International ed. in English) · 2025Article
- Catalytic Enantioselective Smiles Rearrangement Enabled by the Directed Evolution of P450 Radical Aryl Migratases.Journal of the American Chemical Society · 2025Article
- A General Amino-(Hetero)arylation of Simple Olefins with (Hetero)aryl Sulfonamides Enabled by anACS catalysis · 2025Article
- Catalytic Enantioselective Synthesis of 1,4-(Hetero) Dicarbonyl Compounds through α-Carbonyl Umpolung.Journal of the American Chemical Society · 2025Article
- Copper-Catalyzed 1,4-Aminohydroxylation and Aminothiolation of 1,3-Dienes by Carbonyl-Assisted Migration.Chem catalysis · 2024Article
- Photo-induced carboxylation of C(spNature communications · 2024Article
- Dialkylation of CFNature communications · 2024Article
- The merger of electro-reduction and hydrogen bonding activation for a radical Smiles rearrangement.Chemical science · 2024Article
- Domino Conjugate Addition-1,4-Aryl Migration for the Synthesis of α,β-Difunctionalized Amides.JACS Au · 2024Article
- Radical-Mediated α-JACS Au · 2024Article
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6 authors at 2 institutions in 2 countries.
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No grant is acknowledged in the PubMed record.
Abstract
The asymmetric construction of all-carbon quaternary centres within acyclic settings represents a long-standing challenge for synthetic chemists. Alongside polar and radical methods, rearrangement reactions represent an attractive platform, but still broadly applicable methods are in high demand. Here we report an asymmetric, radical sulfinyl-Smiles rearrangement to access acyclic amides that bear an α-all-carbon quaternary centre. Our strategy uses enantioenriched N-arylsulfinyl acrylamides as acceptors for a variety of radicals produced in situ under mild photoredox conditions. The sulfinamido group not only directs the 1,4-migration of the aryl moiety onto the α-carbon of the amide, which thus governs its absolute configuration, but also functions as a traceless chiral auxiliary. The amides obtained in this multicomponent process are prevalent in pharmaceuticals, agrochemicals and bioactive natural products, and can be transformed into valuable chiral α,α-disubstituted acids, oxindoles as well as into β,β-disubstituted amines, highlighting the synthetic potential of this transformation.
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