ArticleThe Journal of organic chemistry2013
Mechanistic analysis and optimization of the copper-catalyzed enantioselective intramolecular alkene aminooxygenation.
Article in The Journal of organic chemistry, 2013. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 16 papers.
What it found
Each row is one number read from the abstract, on the scale the paper reported it, with its interval. Left of the dashed line favours the treatment, right favours the comparator. Under each row is the sentence it came from. New to these charts? A ten-minute tutorial.
The abstract states no effect estimate the extractor could read, or names no intervention and outcome on the map, so this paper lights no cell and moves no belief. It is still indexed, cited and linked below.
The trial behind it
Trials whose registry record cites this paper, or whose number appears in the abstract. A trial that started after this paper was published is citing it as background, not reporting it.
Neither the registry nor the abstract names a trial number. If this is a trial report, that itself is worth knowing.
Who cites it
16 citing papers in PubMed, 74 citations in OpenAlex.
- An Enantioselective Alkene Aminoarylation to Form Chiral Indolines via Electrostatically-Directed Palladium Catalysis.Angewandte Chemie (International ed. in English) · 2026Article
- Incorporating azaheterocycle functionality in intramolecular aerobic, copper-catalyzed aminooxygenation of alkenes.RSC advances · 2024Article
- Radical Cyclization-Initiated Difunctionalization Reactions of Alkenes and Alkynes.Molecules (Basel, Switzerland) · 2024Review
- Copper-catalyzed generation of nitrogen-centered radicals and reactions thereof.ARKIVOC : free online journal of organic chemistry · 2024Article
- Mechanistic Studies of Iron-PyBOX-Catalyzed Olefin Amino-Oxygenation with Functionalized Hydroxylamines.Organometallics · 2023Article
- Copper-Catalyzed Enantioselective Aerobic Alkene Aminooxygenation and Dioxygenation: Access to 2-Formyl Saturated Heterocycles and Unnatural Proline Derivatives.Journal of the American Chemical Society · 2023Article
- Regiodivergent Electrophotocatalytic Aminooxygenation of Aryl Olefins.Journal of the American Chemical Society · 2022Article
- Stereoselective and Regioselective Synthesis of Heterocycles via Copper-Catalyzed Additions of Amine Derivatives and Alcohols to Alkenes.The Journal of organic chemistry · 2017Article
- Stereoselective Synthesis of Isoxazolidines via Copper-Catalyzed Alkene Diamination.ACS catalysis · 2017Article
- Copper-catalyzed intermolecular oxyamination of olefins using carboxylic acids and O-benzoylhydroxylamines.Beilstein journal of organic chemistry · 2016Article
- Copper-Catalyzed Alkene Diamination: Synthesis of Chiral 2-Aminomethyl Indolines and Pyrrolidines.Chemical science · 2014Article
- A computational study of the copper(II)-catalyzed enantioselective intramolecular aminooxygenation of alkenes.The Journal of organic chemistry · 2013Article
- Copper-catalyzed oxidative amination and allylic amination of alkenes.Chemistry (Weinheim an der Bergstrasse, Germany) · 2013Article
- Aerobic copper-catalyzed organic reactions.Chemical reviews · 2013Review
- Chemistry. Copper's contribution to amination catalysis.Science (New York, N.Y.) · 2013Article
- Copper-Catalyzed Synthesis ofSynlett : accounts and rapid communications in synthetic organic chemistryArticle
Corrections and comments
PubMed lists nothing against this paper. Absence here is not a guarantee, only a check that was made.
Authors and funding
3 authors at 1 institution in 1 country.
Funding
Abstract
The catalytic asymmetric aminooxygenation of alkenes provides an efficient and straightforward approach to prepare chiral vicinal amino alcohols. We have reported a copper(II)-catalyzed enantioselective intramolecular alkene aminooxygenation, using (2,2,6,6-tetramethylpiperidin-1-yl)oxyl (TEMPO) as the oxygen source, which results in the synthesis of chiral indolines and pyrrolidines. Herein we disclose that kinetics studies indicate the reaction is first order both in substrate and the [Cu(R,R)-Ph-bis(oxazoline)]OTf(2) catalyst and zero order in TEMPO. Furthermore, kinetic isotope effect studies support that the cis-aminocupration step, the addition of N-Cu across the alkene, is the rate-limiting step. Subsequent formation of a carbon radical intermediate and direct carbon radical trapping with TEMPO is the indicated mechanism for the C-O bond formation as suggested by a deuterium labeling experiment. A ligand screen revealed that C(4)-phenyl substitution on the bis(oxazoline) is optimal for high asymmetric induction. The size of the substrate's N-sulfonyl group also influences the enantioselectivity of the reaction. The preparative-scale catalytic aminooxygenation reaction (gram scale) was demonstrated, and an unexpected dependence on reaction temperature was uncovered on the larger scale reaction.
Indexed as
Identifiers
What OpenQuestion holds
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.