ArticleChem2019
Direct Observation and Analysis of the Halo-Amino-Nitro Alkane Functional Group.
Article in Chem, 2019. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 11 papers.
What it found
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The trial behind it
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Who cites it
11 citing papers in PubMed.
- Recognition of a Conserved Minimal Catalaphile Explains Catalyst Generality in Enantioselective Nitroalkene Reductions.ACS catalysis · 2026Article
- Total Synthesis of Feglymycin Using Umpolung Amide Synthesis.Angewandte Chemie (International ed. in English) · 2025Article
- Elucidating Fluorine Steering Effects in Diels-Alder Reactions Interfaced with Charge-Enhanced Reactivity.European journal of organic chemistry · 2025Article
- Backbone-Determined Antiarrhythmic Structure-Activity Relationships for a Mirror Image, Oligomeric Depsipeptide Natural Product.Journal of medicinal chemistry · 2024Article
- Nitroalkanes as thioacyl equivalents to access thioamides and thiopeptides.Nature communications · 2023Article
- Secondary Orbital Effect Involving Fluorine is Responsible for Substrate-Controlled Diastereodivergence in the Catalyzed syn-aza-Henry Reaction of α-Fluoronitroalkanes.Chemistry (Weinheim an der Bergstrasse, Germany) · 2023Article
- Enantioselective Synthesis ofOrganic letters · 2023Article
- Preparation ofJournal of the American Chemical Society · 2022Article
- Enantioselective iodolactonization to prepare ε-lactone rings using hypervalent iodine.Chemical science · 2022Article
- Umpolung strategies for the functionalization of peptides and proteins.Chemical science · 2022Review
- Fluorine-induced diastereodivergence discovered in an equally rare enantioselectiveChemical science · 2022Article
Corrections and comments
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Authors and funding
6 authors.
Funding
Abstract
Conventional amide synthesis is a mainstay in discipline-spanning applications, and it is a reaction type that historically developed as a singular paradigm when considering the carbon-nitrogen bond-forming step. Umpolung amide synthesis (UmAS) exploits the unique properties of an α-halo nitroalkane in its reaction with an amine to produce an amide. The "umpolung" moniker reflects its paradigm-breaking C-N bond formation on the basis of evidence that the nucleophilic nitronate carbon and electrophilic nitrogen engage to form a tetrahedral intermediate (TI) that is an unprecedented functional group, a 1,1,1-halo-amino-nitro alkane (HANA). Studies probing HANA transience have failed to capture this (presumably) highly reactive intermediate. We report here the direct observation of a HANA, its conversion thermally to an amide functionality, and quantitative analysis of this process using computational techniques. These findings validate the HANA as a functional group common to UmAS and diverted UmAS, opening the door to its targeted use and creative manipulation.
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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.