ArticleThe Journal of organic chemistry2012
Stereoselective isoxazolidine synthesis via copper-catalyzed alkene aminooxygenation.
Article in The Journal of organic chemistry, 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.
- Catalyst-Controlled, Regiodivergent Aminooxygenation Reactions of Dienes.The Journal of organic chemistry · 2026Article
- Incorporating azaheterocycle functionality in intramolecular aerobic, copper-catalyzed aminooxygenation of alkenes.RSC advances · 2024Article
- Article
- 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
- Stereoselective Synthesis of Isoxazolidines via Copper-Catalyzed Alkene Diamination.ACS catalysis · 2017Article
- Crystal structure of (2Acta crystallographica. Section E, Crystallographic communications · 2017Article
- Copper-catalyzed aminooxygenation of styrenes with N-fluorobenzenesulfonimide and N-hydroxyphthalimide derivatives.Beilstein journal of organic chemistry · 2015Article
- 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
Corrections and comments
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Authors and funding
3 authors.
Funding
Abstract
Isoxazolidines are useful in organic synthesis, drug discovery, and chemical biology endeavors. A new stereoselective synthesis of methyleneoxy-substituted isoxazolidines is disclosed. The method involves copper-catalyzed aminooxygenation/cyclization of N-sulfonyl-O-butenyl hydroxylamines in the presence of (2,2,6,6-tetramethylpiperidin-1-yl)oxyl radical (TEMPO) and O(2) and provides substituted isoxazolidines in excellent yields and diastereoselectivities. We also demonstrate selective mono N-O reduction followed by oxidation of the remaining N-O bond to reveal a 2-amino-γ-lactone. Reduction of the γ-lactone reveals the corresponding aminodiol.
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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.