Category Ranking
98%
Total Visits
921
Avg Visit Duration
2 minutes
Citations
20
Article Abstract
An efficient procedure for the preparation of β-substituted furans/pyrroles is presented. The methodology is based on the use of 7-oxa/azanorbornadienes as dipolarophiles in 1,3-dipolar cycloaddition with benzyl azide. The triazoline cycloadduct thus formed spontaneously decomposes via a retro-Diels-Alder (rDA) reaction to afford a β-substituted furan/pyrrole derivative and a stable triazole. The scope of this tandem 1,3-dipolar cycloaddition/rDA reaction was studied with thirteen 7-heteronorbornadienes. This study allowed a deep knowledge of the regioselectivity of the reaction, which can be tuned through the substituents of the heteronorbornadienic systems.
Download full-text PDF |
Source |
|---|---|
| http://dx.doi.org/10.1021/acs.joc.0c00810 | DOI Listing |
Publication Analysis
Top Keywords
Similar Publications
Access to Cyclic Aliphatic Sulfonyl Fluorides via Diels-Alder Cycloaddition.
J Org Chem
September 2025
Pharmaron Drug Discovery Services Europe, Pharmaron UK Ltd., West Hill Innovation Park, Hertford Road, Hoddesdon EN11 9FH, United Kingdom.
Sulfur(VI) fluoride exchange (SuFEx) compounds are gaining increasing attention due to their various applications. We present the Diels-Alder reaction of ethenesulfonyl fluoride and analogues to rapidly access cyclic and bicyclic SuFEx derivatives in moderate to good yields. These derivatives have been shown to be useful intermediates in a variety of synthetic transformations to expand the toolkit for the preparation of cyclic aliphatic sulfonyl fluorides.
View Article and Find Full Text PDFDiastereoselective Iron-Catalyzed [4 + 1] Cycloadditions of Imines with Sulfoxonium Ylides Enable Modular Synthesis of Oxazolidin-2-ones: O- versus N-Nucleophilic Attack.
Org Lett
September 2025
Institute of Advanced Synthesis, School of Chemistry and Molecular Engineering, Nanjing Tech University, Nanjing 211816, China.
Presented herein is a protocol for the iron-catalyzed [4 + 1] cycloadditions of -Boc-imines with β-ketosulfoxonum ylides through a succession of nucleophilic additions and intramolecular annulation, giving access to functionalized oxazolidine-2-ones in generally good yields. In contrast to the renown Corey-Chaykovsky reaction via N attack to furnish aziridines, this method afforded oxazolidine-2-ones via an O-nucleophilic attack. Features of this strategy include readily accessible starting materials, sustainable catalyst, post-functionalizations of complex molecules, scalability, and exceptional control over diastereoselectivity.
View Article and Find Full Text PDFChalasoergodimers A-E, heterodimers with multiple polymerization modes from a marine-derived Chaetomium sp. fungus.
Nat Prod Bioprospect
September 2025
College of Pharmaceutical Sciences, Key Laboratory of Medicinal Chemistry and Molecular Diagnostics of Education Ministry of China, State Key Laboratory of New Pharmaceutical Preparations and Excipients, Hebei University, Baoding, 071002, People's Republic of China.
Five new heterodimers, chalasoergodimers A-E (1-5), and three known heterodimers (6-8), along with four chaetoglobosin monomers (9-12), were isolated from a marine-derived Chaetomium sp. fungus. The structures of new compounds 1-5 were elucidated by HRESIMS, NMR, chemical calculated C NMR and ECD methods.
View Article and Find Full Text PDFPrecise Modulation of Zeolite Acidity by Alkali Metal Ions for Enhancing Catalytic Performance in CO Cycloaddition Reactions.
Inorg Chem
September 2025
State Key Laboratory of Inorganic Synthesis and Preparative Chemistry, College of Chemistry, Jilin University, Changchun 130021, P. R. China.
The CO cycloaddition route is an effective way to achieve efficient conversion and utilization of CO. Zeolites with diverse topologies and tunable acidic sites can efficiently promote the cycloaddition reaction of CO with epoxides. The exchangeable cations in zeolites have a great influence on the performance of the CO cycloaddition, but there are few studies on it.
View Article and Find Full Text PDFDevelopment of Cyclooctyne-Nitrone Based Click Release Chemistry for Bioorthogonal Prodrug Activation both and .
J Am Chem Soc
September 2025
Center of Drug Discovery, State Key Laboratory of Natural Medicine, China Pharmaceutical University, Nanjing 211198, China.
The advancement of bioorthogonal cleavage platforms has emerged as a critical frontier in chemical biology, offering precise molecular liberation through physiologically compatible activation mechanisms. Despite its significant potential, ensuring efficacy typically requires rapid reaction kinetics, high-efficiency payload release, and stable reactants; however, relevant reports remain sparse. Herein, we developed a strain-promoted alkyne-nitrone cycloaddition (SPANC)-based click-release chemistry through installation of a carbamate-linked release moiety at the propargyl position of cyclooctyne, triggering a spontaneous elimination following click cycloaddition to achieve efficient payload liberation.
View Article and Find Full Text PDF