ArticleOrganic letters2014
Umpolung amide synthesis using substoichiometric N-iodosuccinimide (NIS) and oxygen as a terminal oxidant.
Article in Organic letters, 2014. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 16 papers.
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Who cites it
16 citing papers in PubMed, 44 citations in OpenAlex.
- Small Molecule Catalyst for Peptide Synthesis.Journal of the American Chemical Society · 2025Article
- Chemoselective synthesis of 1,3,4-thiadiazoles from acyl hydrazines and nitroalkanes using elemental sulfur.Nature communications · 2025Article
- Generality-Driven Catalyst Development: A Universal Catalyst for Enantioselective Nitroalkene Reduction.Journal of the American Chemical Society · 2024Article
- RyR2 Binding of an Antiarrhythmic Cyclic Depsipeptide Mapped Using Confocal Fluorescence Lifetime Detection of FRET.ACS chemical biology · 2023Article
- Nitroalkanes as thioacyl equivalents to access thioamides and thiopeptides.Nature communications · 2023Article
- Preparation ofJournal of the American Chemical Society · 2022Article
- Umpolung strategies for the functionalization of peptides and proteins.Chemical science · 2022Review
- Fluorine-induced diastereodivergence discovered in an equally rare enantioselectiveChemical science · 2022Article
- The Formation of Impossible Rings in Macrocyclooligomerizations for Cyclodepsipeptide Synthesis: The 18-from-12 Paradox.The Journal of organic chemistry · 2021Article
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- The inverted ketene synthon: a double umpolung approach to enantioselective βChemical science · 2019Article
- A convergent synthesis of 1,3,4-oxadiazoles from acyl hydrazides under semiaqueous conditions.Chemical science · 2017Article
- Organocatalytic Insertion of Isatins into Aryl Difluoronitromethyl Ketones.The Journal of organic chemistry · 2017Article
- Synthesis of α-amino acid derivatives and peptides via enantioselective addition of masked acyl cyanides to imines.Journal of the American Chemical Society · 2014Article
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Corrections and comments
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Authors and funding
5 authors at 1 institution in 1 country.
Funding
Abstract
Umpolung Amide Synthesis (UmAS) provides direct access to amides from an α-bromo nitroalkane and an amine. Based on its mechanistic bifurcation after convergent C-N bond formation, depending on the absence or presence of oxygen, UmAS using substoichiometric N-iodosuccinimide (NIS) under aerobic conditions has been developed. In combination with the enantioselective preparation of α-bromo nitroalkane donors, this protocol realizes the goal of enantioselective α-amino amide and peptide synthesis based solely on catalytic methods.
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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.