ArticleProceedings of the National Academy of Sciences of the United States of America2012
Discovery of competing anaerobic and aerobic pathways in umpolung amide synthesis allows for site-selective amide 18O-labeling.
Article in Proceedings of the National Academy of Sciences of the United States of America, 2012. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 20 papers.
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Who cites it
20 citing papers in PubMed, 47 citations in OpenAlex.
- Total Synthesis of Feglymycin Using Umpolung Amide Synthesis.Angewandte Chemie (International ed. in English) · 2025Article
- Backbone-Determined Antiarrhythmic Structure-Activity Relationships for a Mirror Image, Oligomeric Depsipeptide Natural Product.Journal of medicinal chemistry · 2024Article
- Generality-Driven Catalyst Development: A Universal Catalyst for Enantioselective Nitroalkene Reduction.Journal of the American Chemical Society · 2024Article
- Nitroalkanes as thioacyl equivalents to access thioamides and thiopeptides.Nature communications · 2023Article
- Umpolung strategies for the functionalization of peptides and proteins.Chemical science · 2022Review
- Fluorine-induced diastereodivergence discovered in an equally rare enantioselectiveChemical science · 2022Article
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- The inverted ketene synthon: a double umpolung approach to enantioselective βChemical science · 2019Article
- 1,3,4-Oxadiazole and Heteroaromatic-Fused 1,2,4-Triazole Synthesis using Diverted Umpolung Amide Synthesis.Synthesis · 2017Article
- A convergent synthesis of 1,3,4-oxadiazoles from acyl hydrazides under semiaqueous conditions.Chemical science · 2017Article
- Enantioselective Synthesis of α-Bromonitroalkanes for Umpolung Amide Synthesis: Preparation ofOrganic syntheses; an annual publication of satisfactory methods for the preparation of organic chemicals · 2016Article
- Synthesis of α-amino acid derivatives and peptides via enantioselective addition of masked acyl cyanides to imines.Journal of the American Chemical Society · 2014Article
- Umpolung amide synthesis using substoichiometric N-iodosuccinimide (NIS) and oxygen as a terminal oxidant.Organic letters · 2014Article
- Organocatalytic, diastereo- and enantioselective synthesis of nonsymmetric cis-stilbene diamines: a platform for the preparation of single-enantiomer cis-imidazolines for protein-protein inhibition.The Journal of organic chemistry · 2014Article
- Silyl imine electrophiles in enantioselective catalysis: a Rosetta Stone for peptide homologation, enabling diverse N-protected aryl glycines from aldehydes in three steps.Organic letters · 2014Article
- Enantioselective synthesis of α-oxy amides via Umpolung amide synthesis.Journal of the American Chemical Society · 2012Article
- Achiral counterion control of enantioselectivity in a Brønsted acid-catalyzed iodolactonization.Journal of the American Chemical Society · 2012Article
- Preparation of H,(4) PyrrolidineQuin-BAM (PBAM).Organic syntheses; an annual publication of satisfactory methods for the preparation of organic chemicals · 2012Article
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Corrections and comments
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Authors and funding
3 authors at 2 institutions in 1 country.
Funding
Abstract
The mechanism of umpolung amide synthesis was probed by interrogating potential sources for the oxygen of the product amide carbonyl that emanates from the α-bromo nitroalkane substrate. Using a series of (18)O-labeled substrates and reagents, evidence is gathered to advance two pathways from the putative tetrahedral intermediate. Under anaerobic conditions, a nitro-nitrite isomerization delivers the amide oxygen from nitro oxygen. The same homolytic nitro-carbon fragmentation can be diverted by capture of the carbon radical intermediate with oxygen gas (O(2)) to deliver the amide oxygen from O(2). This understanding was used to develop a straightforward protocol for the preparation of (18)O-labeled amides in peptides by simply performing the umpolung amide synthesis reaction under an atmosphere of 18O2.
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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.