ArticleOrganic letters2009
Diastereoselective pyrrolidine synthesis via copper promoted intramolecular aminooxygenation of alkenes: formal synthesis of (+)-monomorine.
Article in Organic letters, 2009. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 24 papers.
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Who cites it
24 citing papers in PubMed.
- Incorporating azaheterocycle functionality in intramolecular aerobic, copper-catalyzed aminooxygenation of alkenes.RSC advances · 2024Article
- Halonium Catalysis: An Underutilized and Underexplored Catalytic Concept in Olefin Functionalizations.Synlett : accounts and rapid communications in synthetic organic chemistry · 2021Article
- Stereoselective and Regioselective Synthesis of Heterocycles via Copper-Catalyzed Additions of Amine Derivatives and Alcohols to Alkenes.The Journal of organic chemistry · 2017Article
- Direct Synthesis of 2-Formylpyrrolidines, 2-Pyrrolidinones and 2-Dihydrofuranones via Aerobic Copper-Catalyzed Aminooxygenation and Dioxygenation of 4-Pentenylsulfonamides and 4-Pentenylalcohols.Journal of the American Chemical Society · 2017Article
- Alkylation of Sulfonamides with Trichloroacetimidates under Thermal Conditions.The Journal of organic chemistry · 2016Article
- Practical Synthetic Procedures for the Iron-Catalyzed Intermolecular Olefin Aminohydroxylation Using Functionalized Hydroxylamines.Synthesis · 2016Article
- Copper(II)-Promoted Cyclization/Difunctionalization of Allenols and Allenylsulfonamides: Synthesis of Heterocycle-Functionalized Vinyl Carboxylate Esters.Organic letters · 2015Article
- Copper-promoted synthesis of 1,4-benzodiazepinones via alkene diamination.Tetrahedron letters · 2015Article
- Copper-catalyzed aminooxygenation of styrenes with N-fluorobenzenesulfonimide and N-hydroxyphthalimide derivatives.Beilstein journal of organic chemistry · 2015Article
- Iron(II)-catalyzed intermolecular amino-oxygenation of olefins through the N-O bond cleavage of functionalized hydroxylamines.Journal of the American Chemical Society · 2014Article
- A computational study of the copper(II)-catalyzed enantioselective intramolecular aminooxygenation of alkenes.The Journal of organic chemistry · 2013Article
- Aerobic copper-catalyzed organic reactions.Chemical reviews · 2013Review
- Mechanistic analysis and optimization of the copper-catalyzed enantioselective intramolecular alkene aminooxygenation.The Journal of organic chemistry · 2013Article
- Stereoselective synthesis of morpholines via copper-promoted oxyamination of alkenes.Organic letters · 2012Article
- Stereoselective isoxazolidine synthesis via copper-catalyzed alkene aminooxygenation.The Journal of organic chemistry · 2012Article
- Iron catalyzed asymmetric oxyamination of olefins.Journal of the American Chemical Society · 2012Article
- Stereoselective synthesis of cis-2,5-disubstituted pyrrolidines via Wacker-type aerobic oxidative cyclization of alkenes with tert-butanesulfinamide nucleophiles.Organic letters · 2012Article
- Evidence for alkene cis-aminocupration, an aminooxygenation case study: kinetics, EPR spectroscopy, and DFT calculations.Chemistry (Weinheim an der Bergstrasse, Germany) · 2012Article
- Stereoselective Copper-Catalyzed Intramolecular Alkene Aminooxygenation: Effects of Substrate and Ligand Structure on Selectivity.European journal of organic chemistry · 2011Article
- Evolution of copper(II) as a new alkene amination promoter and catalyst.Journal of organometallic chemistry · 2011Article
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2 authors.
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Abstract
The diastereoselectivity of the copper-promoted intramolecular aminooxygenation of various alkene substrates was investigated. Alpha-substituted 4-pentenyl sulfonamides favor the formation of 2,5-cis-pyrrolidines (dr >20:1) giving excellent yields which range from 76-97% while gamma-substituted substrates favor the 2,3-trans pyrrolidine adducts with moderate selectivity (ca. 3:1). A substrate whose N-substituent was directly tethered to the alpha-carbon exclusively yielded the 2,5-trans pyrrolidine. The synthetic utility of the method was demonstrated by a short and efficient formal synthesis of (+)-monomorine.
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