ArticleJournal of the American Chemical Society2019
α-Functionalization of Cyclic Secondary Amines: Lewis Acid Promoted Addition of Organometallics to Transient Imines.
Article in Journal of the American Chemical Society, 2019. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 37 papers.
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Who cites it
37 citing papers in PubMed, 120 citations in OpenAlex.
- Deciphering competing reaction pathways in the α-C-H functionalization of unprotected alicyclic aminesOrganic chemistry frontiers : an international journal of organic chemistry · 2026Article
- An alkyl-swap platform for late-stage modification of secondary N-methylamines.Nature chemistry · 2026Article
- Recent Developments in Azomethine Ylide-Initiated Double Cycloadditions.Molecules (Basel, Switzerland) · 2025Review
- Cyclic Imine-BFSynlett : accounts and rapid communications in synthetic organic chemistry · 2025Article
- Computational and Experimental Studies on the α-Functionalization of Ketones Using Domino Reactions: A Strategy to Increase Chemoselectivity at the α-Carbon of Ketones.Molecules (Basel, Switzerland) · 2025Article
- Photocatalytic Decarboxylative Alkylation of Cyclic Imine-BFJournal of the American Chemical Society · 2024Article
- Stereocontrolled and time-honored access to piperidine- and pyrrolidine-fused 3-methylenetetrahydropyrans using lactam-tethered alkenols.RSC advances · 2024Article
- Regioselective α-Phosphonylation of Unprotected Alicyclic Amines.Organic letters · 2024Article
- Synthetic techniques for thermodynamically disfavoured substituted six-membered rings.Nature reviews. Chemistry · 2024Review
- Copper-Nitroxyl-Catalyzed α-Oxygenation of Cyclic Secondary Amines Including Application to Late-Stage Functionalization.Journal of the American Chemical Society · 2024Article
- Oxidative Dearomatization of Pyridines.Journal of the American Chemical Society · 2024Article
- Alicyclic-Amine-Derived Imine-BFAngewandte Chemie (International ed. in English) · 2024Article
- Synthesis of dienes from pyrrolidines using skeletal modification.Nature communications · 2023Article
- Palladium-Catalyzed Arylation of Endocyclic 1-Azaallyl Anions: Concise Synthesis of Unprotected Enantioenriched cis-2,3-Diarylpiperidines.Angewandte Chemie (International ed. in English) · 2023Article
- Article
- Transannular Functionalization of Multiple C(spOrganometallics · 2023Article
- Understanding and Circumventing the Requirement for Native Thioester Substrates for α-Oxoamine Synthase Reactions.ACS chemical biology · 2022Article
- Regioselective α-Cyanation of Unprotected Alicyclic Amines.Organic letters · 2022Article
- Catalytic Lewis Base Additive Enables Selective Copper-Catalyzed Borylative α-C-H Allylation of Alicyclic Amines.Journal of the American Chemical Society · 2022Article
- Synthesis of Polycyclic Isoindolines via α-C-H/N-H Annulation of Alicyclic Amines.Organic letters · 2022Article
Corrections and comments
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Authors and funding
2 authors at 1 institution in 1 country.
Funding
Abstract
Cyclic imines, generated in situ from their corresponding N-lithiated amines and a ketone hydride acceptor, undergo reactions with a range of organometallic nucleophiles to generate α-functionalized amines in a single operation. Activation of the transient imines by Lewis acids that are compatible with the presence of lithium alkoxides was found to be crucial to accommodate a broad range of nucleophiles including lithium acetylides, Grignard reagents, and aryllithiums with attenuated reactivities.
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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.