ArticleJournal of the American Chemical Society2016
Chemo- and Stereoselective Transition-Metal-Free Amination of Amides with Azides.
Article in Journal of the American Chemical Society, 2016. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 22 papers.
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Who cites it
22 citing papers in PubMed, 127 citations in OpenAlex.
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- α-Amination of 1,3-Dicarbonyl Compounds and Analogous Reactive Enolate-Precursors Using Ammonia under Oxidative Conditions.Angewandte Chemie (International ed. in English) · 2025Article
- PyrAtes: Modular Organic Salts with Large Stokes Shifts for Fluo-rescence Microscopy.Angewandte Chemie (International ed. in English) · 2024Article
- Free Amino Group Transfer via α-Amination of Native Carbonyls.Angewandte Chemie (International ed. in English) · 2023Article
- Transfer freier Aminogruppen via α-Aminierung von Carbonylen.Angewandte Chemie (Weinheim an der Bergstrasse, Germany) · 2023Article
- Chemoselektive γ-Oxidation von β,γ-ungesättigten Amiden mit TEMPO.Angewandte Chemie (Weinheim an der Bergstrasse, Germany) · 2021Article
- Chemoselective γ-Oxidation of β,γ-Unsaturated Amides with TEMPO.Angewandte Chemie (International ed. in English) · 2021Article
- Chemoselective α-Sulfidation of Amides Using Sulfoxide Reagents.Organic letters · 2020Article
- Entropic Mixing Allows Monomeric-Like Absorption in Neat BODIPY Films.Chemistry (Weinheim an der Bergstrasse, Germany) · 2020Article
- A Novel Class of 7-Membered Heterocyclic Compounds.European journal of organic chemistry · 2020Article
- Synthesis of Novel Heterocycles by Amide Activation and Umpolung Cyclization.Organic letters · 2020Article
- Unified Approach to the Chemoselective α-Functionalization of Amides with Heteroatom Nucleophiles.Journal of the American Chemical Society · 2019Article
- Synthesis of γ-substituted carbonyl compounds from DMSO-mediated oxidation of enynamides: mechanistic insights and carbon- and hetero-functionalizations.Chemical science · 2019Article
- Chemoselective α,β-Dehydrogenation of Saturated Amides.Angewandte Chemie (International ed. in English) · 2019Article
- Iridium-catalyzed reductive Ugi-type reactions of tertiary amides.Nature communications · 2018Article
- Cross-coupling of dissimilar ketone enolates via enolonium species to afford non-symmetrical 1,4-diketones.Beilstein journal of organic chemistry · 2018Article
- Regioselective synthesis of pyridines by redox alkylation of pyridineMonatshefte fur chemie · 2018Article
- Chemoselective Intermolecular Cross-Enolate-Type Coupling of Amides.Journal of the American Chemical Society · 2017Article
- Mild Reductive Functionalization of Amides intoChemistryOpen · 2017Article
- Mechanistic Pathways in Amide Activation: Flexible Synthesis of Oxazoles and Imidazoles.Organic letters · 2017Article
Corrections and comments
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Authors and funding
6 authors at 1 institution in 1 country.
Funding
Abstract
The synthesis of α-amino carbonyl/carboxyl compounds is a contemporary challenge in organic synthesis. Herein, we present a stereoselective α-amination of amides employing simple azides that proceeds under mild conditions with release of nitrogen gas. The amide is used as the limiting reagent, and through simple variation of the azide pattern, various differently substituted aminated products can be obtained. The reaction is fully chemoselective for amides even in the presence of esters or ketones and lends itself to preparation of optically enriched products.
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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.