ArticleOrganic letters2012
A peptide-embedded trifluoromethyl ketone catalyst for enantioselective epoxidation.
Article in Organic letters, 2012. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 10 papers.
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Who cites it
10 citing papers in PubMed.
- Stereospecific Radical Bromination of β-Aryl Alcohols with Thiourea Additives Through A Serendipitous Discovery of A 1,2-Aryl Migration.Chemistry (Weinheim an der Bergstrasse, Germany) · 2025Article
- Organocatalytic activation of hydrogen peroxide: towards green and sustainable oxidations.Chemical science · 2024Review
- Stereoselective peptide catalysis in complex environments - from river water to cell lysates.Chemical science · 2022Article
- Asymmetric Catalysis Mediated by Synthetic Peptides, Version 2.0: Expansion of Scope and Mechanisms.Chemical reviews · 2020Review
- A Bottom Up Approach Towards Artificial Oxygenases by Combining Iron Coordination Complexes and Peptides.Chemical science · 2017Article
- Synthesis and evaluation of phenylalanine-derived trifluoromethyl ketones for peptide-based oxidation catalysis.Bioorganic & medicinal chemistry · 2016Article
- Enantioselective synthesis of 3-arylquinazolin-4(3H)-ones via peptide-catalyzed atroposelective bromination.Journal of the American Chemical Society · 2015Article
- Function-Oriented Investigations of a Peptide-Based Catalyst that Mediates Enantioselective Allylic Alcohol Epoxidation.Chemical science · 2014Article
- Tungsten-catalyzed asymmetric epoxidation of allylic and homoallylic alcohols with hydrogen peroxide.Journal of the American Chemical Society · 2014Article
- Enhanced reactivity in dioxirane C-H oxidations via strain release: a computational and experimental study.The Journal of organic chemistry · 2013Article
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Authors and funding
2 authors.
Funding
Abstract
The development of peptide-based oxidation catalysts that use a transiently generated dioxirane as the chemically active species is reported. The active catalyst is a chiral trifluoromethyl ketone (Tfk) with a pendant carboxylic acid that can be readily incorporated into a peptide. These peptides were capable of epoxidizing alkenes in high yield (up to 89%) and enantiomeric ratios (er) ranging from 69.0:31.0 to 91.0:9.0, depending on the alkene substitution pattern.
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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.