ArticleJournal of the American Chemical Society2017
Direct Synthesis of 2-Formylpyrrolidines, 2-Pyrrolidinones and 2-Dihydrofuranones via Aerobic Copper-Catalyzed Aminooxygenation and Dioxygenation of 4-Pentenylsulfonamides and 4-Pentenylalcohols.
Article in Journal of the American Chemical Society, 2017. 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.
- Recent Advances in Intramolecular C─N Bond Formation for Pyrrolidine Synthesis.ChemistryOpen · 2026Review
- Incorporating azaheterocycle functionality in intramolecular aerobic, copper-catalyzed aminooxygenation of alkenes.RSC advances · 2024Article
- Cobalt-Catalyzed Aerobic Aminocyclization of Unsaturated Amides for the Synthesis of Functionalized γ- and δ-Lactams.Organic letters · 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
- Copper(I)-Catalyzed Cross-Coupling of 1-Bromoalkynes with N-Heterocyclic Organozinc Reagents.Molecules (Basel, Switzerland) · 2022Article
- Mn- and Co-Catalyzed Aminocyclizations of Unsaturated Hydrazones Providing a Broad Range of Functionalized Pyrazolines.JACS Au · 2021Article
- Enantioselective, Aerobic Copper-Catalyzed Intramolecular Carboamination and Carboetherification of Unactivated Alkenes.ACS catalysis · 2020Article
- Desaturation via Redox-Neutral Hydrogen Transfer Process: Synthesis of 2-Allyl Anilines, Mechanism and Applications.iScience · 2020Article
- Preparation of cyclic imides from alkene-tethered amides: application of homogeneous Cu(ii) catalytic systems.RSC advances · 2020Article
- Stereoselective and Regioselective Synthesis of Heterocycles via Copper-Catalyzed Additions of Amine Derivatives and Alcohols to Alkenes.The Journal of organic chemistry · 2017Article
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2 authors.
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Abstract
A new method for the direct conversion of 4-pentenylsulfonamides to 2-formylpyrrolidines and a 2-ketopyrrolidine has been developed. This transformation occurs via aerobic copper-catalyzed alkene aminooxygenation where molecular oxygen serves as both oxidant and oxygen source. The 2-formylpyrrolidines can further undergo oxidative carbon-carbon bond cleavage in situ upon addition of DABCO, providing 2-pyrrolidinones. These transformations have been demonstrated for a range of 4-pentenylsulfonamides. 4-Pentenylalcohols also undergo oxidative cyclization to form γ-lactones predominantly. The reaction is chemoselective, oxidizing one alkene in the presence of others, and is compatible with several functional groups. Application of these reactions to the formal syntheses of baclofen and (+)-monomorine was demonstrated.
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