ArticleJournal of the American Chemical Society2023
Scope and Mechanistic Probe into Asymmetric Synthesis of α-Trisubstituted-α-Tertiary Amines by Rhodium Catalysis.
Article in Journal of the American Chemical Society, 2023. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 9 papers.
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Who cites it
9 citing papers in PubMed, 16 citations in OpenAlex.
- Cobalt-Catalyzed Radical Ligand Transfer (RLT) Enables Remote-Markovnikov Hydroamination of Alkenes.Angewandte Chemie (International ed. in English) · 2026Article
- Article
- Rhodium-Catalyzed Allylic Amination for the Enantioselective Synthesis of Tertiary β-Fluoroamines.Organic letters · 2025Article
- Cooperative Catalysis in StereoselectiveJournal of the American Chemical Society · 2024Article
- Photochemical 1,3-boronate rearrangement enables three-component N-alkylation for α-tertiary hydroxybenzylamine synthesis.Nature communications · 2024Article
- Regio- and enantioselective nickel-alkyl catalyzed hydroalkylation of alkynes.Nature communications · 2024Article
- Copper catalysed asymmetric amination.Nature chemistry · 2024Article
- Enantioselective propargylic amination and related tandem sequences to α-tertiary ethynylamines and azacycles.Nature chemistry · 2024Article
- Rhodium-Catalyzed Asymmetric Synthesis of 1,2-Disubstituted Allylic Fluorides.Angewandte Chemie (International ed. in English) · 2023Article
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Authors and funding
4 authors at 1 institution in 1 country.
Funding
Abstract
Asymmetric reactions that convert racemic mixtures into enantioenriched amines are of significant importance due to the prevalence of amines in pharmaceuticals, with about 60% of drug candidates containing tertiary amines. Although transition-metal catalyzed allylic substitution processes have been developed to provide access to enantioenriched α-disubstituted allylic amines, enantioselective synthesis of sterically demanding α-tertiary amines with a tetrasubstituted carbon stereocenter remains a major challenge. Herein, we report a chiral diene-ligated rhodium-catalyzed asymmetric substitution of racemic tertiary allylic trichloroacetimidates with aliphatic secondary amines to afford α-trisubstituted-α-tertiary amines. Mechanistic investigation is conducted using synergistic experimental and computational studies. Density functional theory calculations show that the chiral diene-ligated rhodium promotes the ionization of tertiary allylic substrates to form both
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