ArticleChemistry (Weinheim an der Bergstrasse, Germany)2020
Chemoselective Alpha-Deuteration of Amides via Retro-ene Reaction.
Article in Chemistry (Weinheim an der Bergstrasse, Germany), 2020. 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, 31 citations in OpenAlex.
- Divergent C2 functionalization of N-Heteroarenes via nonclassical rearomatization.Nature communications · 2026Article
- Asymmetric Synthesis of β-Ketoamides by Sulfonium Rearrangement.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
- Challenges and Breakthroughs in Selective Amide Activation.Angewandte Chemie (International ed. in English) · 2022Review
- Challenges and Breakthroughs in Selective Amide Activation.Angewandte Chemie (Weinheim an der Bergstrasse, Germany) · 2022Review
- Controlled Tetradeuteration of Straight-Chain Fatty Acids: Synthesis, Application, and Insight into the Metabolism of Oxidized Linoleic Acid.Angewandte Chemie (International ed. in English) · 2022Article
- Direct Synthesis of Enamides via Electrophilic Activation of Amides.Journal of the American Chemical Society · 2021Article
- Chemoselective Alpha-Deuteration of Amides via Retro-ene Reaction.Chemistry (Weinheim an der Bergstrasse, Germany) · 2020Article
Corrections and comments
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Authors and funding
5 authors at 1 institution in 1 country.
Funding
Abstract
A synthetically convenient approach for the direct α-deuteration of amides is reported. This mechanistically unusual process relies on a retro-ene-type process, triggered by the addition of deuterated dimethyl sulfoxide to a keteniminium intermediate, generated through electrophilic amide activation. The transformation displays broad functional-group tolerance and high deuterium incorporation.
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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.