ArticleJournal of the American Chemical Society2012
Enantioselective synthesis of α-oxy amides via Umpolung amide synthesis.
Article in Journal of the American Chemical Society, 2012. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 19 papers.
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Who cites it
19 citing papers in PubMed, 66 citations in OpenAlex.
- Photochemical deracemization of α-chiral carboxamides mediated by inter- and intramolecular hydrogen bonding.Chemical science · 2026Article
- 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
- RyR2 Binding of an Antiarrhythmic Cyclic Depsipeptide Mapped Using Confocal Fluorescence Lifetime Detection of FRET.ACS chemical biology · 2023Article
- Preparation ofJournal of the American Chemical Society · 2022Article
- Umpolung strategies for the functionalization of peptides and proteins.Chemical science · 2022Review
- The Formation of Impossible Rings in Macrocyclooligomerizations for Cyclodepsipeptide Synthesis: The 18-from-12 Paradox.The Journal of organic chemistry · 2021Article
- Further Developments and Applications of Oxazoline-Containing Ligands in Asymmetric Catalysis.Chemical reviews · 2021Article
- An umpolung strategy to react catalytic enols with nucleophiles.Nature communications · 2019Article
- Biomimetic catalytic transformation of toxic α-oxoaldehydes to high-value chiral α-hydroxythioesters using artificial glyoxalase I.Nature communications · 2017Article
- A convergent synthesis of 1,3,4-oxadiazoles from acyl hydrazides under semiaqueous conditions.Chemical science · 2017Article
- Rapid synthesis of cyclic oligomeric depsipeptides with positional, stereochemical, and macrocycle size distribution control.Proceedings of the National Academy of Sciences of the United States of America · 2016Article
- Enantioselective Synthesis of β-Fluoro Amines via β-Amino α-Fluoro Nitroalkanes and a Traceless Activating Group Strategy.Journal of the American Chemical Society · 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
- 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
- Squaramide-catalyzed enantioselective Michael addition of masked acyl cyanides to substituted enones.Journal of the American Chemical Society · 2013Article
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Authors and funding
3 authors at 1 institution in 1 country.
Funding
Abstract
α-Oxy amides are prepared through enantioselective synthesis using a sequence beginning with a Henry addition of bromonitromethane to aldehydes and finishing with Umpolung Amide Synthesis (UmAS). Key to high enantioselection is the finding that ortho-iodo benzoic acid salts of the chiral copper(II) bis(oxazoline) catalyst deliver both diastereomers of the Henry adduct with high enantiomeric excess, homochiral at the oxygen-bearing carbon. Overall, this approach to α-oxy amides provides an innovative complement to alternatives that focus almost entirely on the enantioselective synthesis of α-oxy carboxylic acids.
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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.