ArticleNature chemistry2024
Organocatalytic aromatization-promoted umpolung reaction of imines.
Article in Nature chemistry, 2024. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 7 papers.
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Who cites it
7 citing papers in PubMed.
- Asymmetric Reductive Three-Component Annulation Reaction for Constructing Fused N-Heterocycles With Contiguous Stereogenic Centers.Angewandte Chemie (International ed. in English) · 2026Article
- Skeletal Editing via Diastereoselective Ring Expansion Enables Enantioenriched Tetrasubstituted ΔJACS Au · 2026Article
- Integrating the Substituent Effect into the Wade-Mingos Rules for Dicarboranes.Angewandte Chemie (International ed. in English) · 2025Article
- Mechanistic Pathways in Cyanide-Mediated Benzoin Condensation: A Comprehensive Electron Localisation Function (ELF) and Catastrophe Theory Analysis of the Umpolung Reaction.Molecules (Basel, Switzerland) · 2025Article
- Divergent Synthesis of Chiroptical Molecular Switches Based on 1,2-Diaxial Atropisomers.JACS Au · 2024Article
- Catalytic kinetic resolution of helical polycyclic phenols via an organocatalyzed enantioselective dearomative amination reaction.Science advances · 2024Article
- Recent Advances in the Domino Annulation Reaction of Quinone Imines.Molecules (Basel, Switzerland) · 2024Review
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Authors and funding
9 authors.
Funding
Abstract
The umpolung functionalization of imines bears vast synthetic potential, but polarity inversion is less efficient compared with the carbonyl counterparts. Strong nucleophiles are often required to react with the N-electrophiles without catalytic and stereochemical control. Here we show an effective strategy to realize umpolung of imines promoted by organocatalytic aromatization. The attachment of strongly electron-withdrawing groups to imines could enhance the umpolung reactivity by both electronegativity and aromatic character, enabling the direct amination of (hetero)arenes with good efficiencies and stereoselectivities. Additionally, the application of chiral Brønsted acid catalyst furnishes (hetero)aryl C-N atropisomers or enantioenriched aliphatic amines via dearomative amination from N-electrophilic aromatic precursors. Control experiments and density functional theory calculations suggest an ionic mechanism for the umpolung reaction of imines. This disconnection expands the options to forge C-N bonds stereoselectively on (hetero)arenes, which represents an important synthetic pursuit, especially in medicinal chemistry.
Identifiers
38062248What OpenQuestion holds
Registered trials
Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the OpenQuestion graph.