ArticleThe Journal of organic chemistry2013
Palladium-catalyzed intermolecular aminoacetoxylation of alkenes and the influence of PhI(OAc)2 on aminopalladation stereoselectivity.
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 13 papers.
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Who cites it
13 citing papers in PubMed.
- NJACS Au · 2024Article
- Pd(II)-Catalyzed Aminoacetoxylation of Alkenes Via Tether Formation.Organic letters · 2022Article
- Palladium-Catalyzed Organic Reactions Involving Hypervalent Iodine Reagents.Molecules (Basel, Switzerland) · 2022Review
- Hypervalent Iodine Reagents in Palladium-Catalyzed Oxidative Cross-Coupling Reactions.Frontiers in chemistry · 2020Review
- Directed, Palladium(II)-Catalyzed Intermolecular Aminohydroxylation of Alkenes Using a Mild Oxidation System.Organic letters · 2018Article
- Palladium-catalysed anti-Markovnikov selective oxidative amination.Nature chemistry · 2018Article
- Palladium-Catalyzed Aerobic Intramolecular Aminoacetoxylation of Alkenes Enabled by Catalytic Nitrate.Organic letters · 2016Article
- Synthesis of 2,3-Dihydrobenzofurans via the Palladium Catalyzed Carboalkoxylation of 2-Allylphenols.Organic chemistry frontiers : an international journal of organic chemistry · 2016Article
- Asymmetric Palladium-Catalyzed Alkene Carboamination Reactions for the Synthesis of Cyclic Sulfamides.Chemistry (Weinheim an der Bergstrasse, Germany) · 2016Article
- Palladium-Catalyzed Alkene Carboamination Reactions of Electron-Poor Nitrogen Nucleophiles.Advanced synthesis & catalysis · 2015Article
- The syn/anti-dichotomy in the palladium-catalyzed addition of nucleophiles to alkenes.Chemistry (Weinheim an der Bergstrasse, Germany) · 2015Article
- Influence of catalyst structure and reaction conditions on anti- versus syn-aminopalladation pathways in Pd-catalyzed alkene carboamination reactions of N-allylsulfamides.Chemistry (Weinheim an der Bergstrasse, Germany) · 2014Article
- Synthesis of vicinal aminoalcohols by stereoselective aza-Wacker cyclizations: access to (-)-acosamine by redox relay.Angewandte Chemie (International ed. in English) · 2013Article
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6 authors.
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Abstract
A modified protocol has been identified for Pd-catalyzed intermolecular aminoacetoxylation of terminal and internal alkenes that enables the alkene to be used as the limiting reagent. The results prompt a reassessment of the stereochemical course of these reactions. X-ray crystallographic characterization of two of the products, together with isotopic labeling studies, show that the amidopalladation step switches from a cis-selective process under aerobic conditions to a trans-selective process in the presence of diacetoxyiodobenzene.
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