ArticleChem2019
Chiral piperidines from acyclic amines via enantioselective, radical-mediated δ C-H cyanation.
Article in Chem, 2019. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 29 papers.
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Who cites it
29 citing papers in PubMed, 134 citations in OpenAlex.
- Remote Desaturation of Unprotected Amines and C─H Amination of Alkanes by Polarity-Matched N-Radical Cations.Angewandte Chemie (International ed. in English) · 2026Article
- Radical Sampling Enabled Saturated N-Heterocycle Cyclization.Journal of the American Chemical Society · 2026Article
- Ligand-controlled regiodivergent and enantioselective C-H cyanation of secondary amines.Nature communications · 2026Article
- A reflection on recent advances in organometallic copper(iii) chemistry.Chemical science · 2026Article
- Cooperative Brønsted Acid and Photo-Promoted Stereoselective Synthesis of Substituted Piperidones.Angewandte Chemie (International ed. in English) · 2025Article
- Facile and Practical Synthesis of Substituted Piperidine-2,6-Diones Under Transition-Metal Free Condition.ChemistryOpen · 2025Article
- Direct stereoselective C(spNature chemistry · 2025Article
- Synthesis and crystal structure of piperidinyl propanenitrile towards the preparation of piperidine based bioactive films for drug delivery applications.Scientific reports · 2025Article
- Chiral pyrrolidines via an enantioselective Hofmann-Löffler-Freytag reaction.Chem catalysis · 2024Article
- Overcoming Copper Reduction Limitation in Asymmetric Substitution: Aryl-Radical-Enabled Enantioconvergent Cyanation of Alkyl Iodides.Journal of the American Chemical Society · 2024Article
- A facile synthesis of α,β-unsaturated imines via palladium-catalyzed dehydrogenation.Nature communications · 2024Article
- Copper-catalyzed generation of nitrogen-centered radicals and reactions thereof.ARKIVOC : free online journal of organic chemistry · 2024Article
- Enantioselective catalytic radical decarbonylative azidation and cyanation of aldehydes.Science advances · 2023Article
- Catalytic Enantioselective Synthesis of 3-Piperidines from Arylboronic Acids and Pyridine.Journal of the American Chemical Society · 2023Article
- Piperidine Derivatives: Recent Advances in Synthesis and Pharmacological Applications.International journal of molecular sciences · 2023Review
- C(spChemical science · 2023Article
- Photoredox catalysis harvesting multiple photon or electrochemical energies.Beilstein journal of organic chemistry · 2023Review
- Divergent regioselective Heck-type reaction of unactivated alkenes and N-fluoro-sulfonamides.Nature communications · 2022Article
- Investigations into mechanism and origin of regioselectivity in the metallaphotoredox-catalyzed α-arylation ofChemical science · 2022Article
- γ C-H Functionalization of Amines via Triple H-Atom Transfer of a Vinyl Sulfonyl Radical Chaperone.Journal of the American Chemical Society · 2022Article
Corrections and comments
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Authors and funding
3 authors at 1 institution in 1 country.
Funding
Abstract
Piperidines are the most prevalent heterocycle found in medicines. Yet, while they are often chiral, there remain no robust methods for their asymmetric syntheses. To solve this challenge, we have interrupted the century-old Hofmann-Löffler-Freytag (HLF) reaction to afford this privileged heterocycle. The catalytic, regio- and enantio- selective δ C-H cyanation of acyclic amines described herein, incorporates a carbonyl equivalent selectively at the δ position. This δ C-H cyanation is enabled by a chiral Cu catalyst, which both initiates and terminates intramolecular hydrogen atom transfer (HAT) by an N-centered radical relay mechanism. The broad scope and utility of this highly enantioselective method for δ C-C formation is presented, as well as conversion of the resulting enantioenriched δ amino nitriles to a family of chiral piperidines. Experiments probing the chemo-, regio-, and enantio- selectivity of this HAT mechanism are also included to enable extension to other stereoselective δ C-H functionalizations.
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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.