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1,3-Dipolar cycloaddition of nonstabilized azomethine ylides derived from α-C-H functionalization of tetrahydroisoquinoline for regio- and diastereoselective synthesis of spirooxindole-pyrrolidines is developed. A three-component reaction of readily available cyclic amine, aryl aldehydes, and olefinic oxindoles provides a pot, atom and step economy (PASE) approach for making spiro-heterocyclic compounds with biological interest.
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http://dx.doi.org/10.1039/d1nj05538k | DOI Listing |
J Org Chem
September 2025
Key Laboratory of Chemical Biology and Traditional Chinese Medicine Research (Ministry of Education), and Key Laboratory of the Assembly and Application of Organic Functional Molecules of Hunan Province, College of Chemistry and Chemical Engineering, Hunan Normal University, Changsha, Hunan 410081,
We herein report a palladium-catalyzed dearomative Heck/C(sp)-H activation/[4 + 2] decarboxylative cyclization of C2-tethered indoles. In this transformation, the alkylpalladium(II) species generated by indole dearomatization undergoes C-H activation to form ,-palladacycles, which are subsequently trapped by -bromobenzoic acids or cyclic β-bromoacrylic acids, enabling regio- and diastereoselective construction of hexacyclic and octocyclic fused indolines with a broad substrate scope.
View Article and Find Full Text PDFAngew Chem Int Ed Engl
September 2025
State Key Laboratory of Green Pesticide, Engineering Research Center of Photoenergy Utilization for Pollution Control and Carbon Reduction, Ministry of Education, College of Chemistry, Central China Normal University (CCNU), 152 Luoyu Road, Wuhan, Hubei, 430079, P.R. China.
Radical-mediated hydroalkylation of alkenes offers a more direct and atom-economical route to α-alkylated carbonyl compounds, enabling the construction of various drug scaffolds, natural products, and functional molecules. However, traditional protocols are generally restricted to active 1,3-dicarbonyl compounds and often require oxidants, large excesses of substrates, and harsh reaction conditions. Herein, we present a photoinduced, general, and practical hydroalkylation of unactivated alkenes with amides.
View Article and Find Full Text PDFJ Org Chem
September 2025
School of Chemistry and Materials Engineering, Anhui Engineering Research Center for Photoelectrocatalytic Electrode Materials, Huainan Normal University, Huainan, Anhui 232038, P. R. China.
Herein, we report a step- and atom-economical allylation reaction of allyl alcohols with activated alkyl bromides by merging cross-electrophile and dehydroxylative coupling under the catalysis of cobalt. This reaction delivers a method to synthesize multisubstituted γ,δ-unsaturated α,α-difluoro amides and carboxylates in a highly regio- and diastereoselective manner. Furthermore, we also demonstrate the viability of a cobalt-catalyzed cross-electrophile desulfonylative allylation in a proof-of-concept study.
View Article and Find Full Text PDFEuropean J Org Chem
August 2024
Department of Chemistry, Vanderbilt University, Nashville, TN 37235, United States.
We describe the first total syntheses of tabernanthine and ibogaline. Entry to these iboga alkaloid natural products is enabled by a thermal coupling of indoles and aziridines to furnish the requisite nosyl tryptamine starting materials. This route features a Friedel-Crafts type alkylation to form the key indole-isoquinuclidine C-C bond.
View Article and Find Full Text PDFOrg Biomol Chem
August 2025
Institute of Pharmaceutical Science and Technology, Collaborative Innovation Center of Yangtze River Delta Region Green Pharmaceuticals, Zhejiang University of Technology, 18 Chaowang Road, Gongshu District, Hangzhou City, Zhejiang Province, China.
A palladium-catalyzed [3 + 2] cycloaddition reaction of vinyl methylene cyclic carbonates with pyrrolidinones was developed. This protocol demonstrates remarkable versatility, enabling the facile construction of diverse [5,5]-spirolactam scaffolds in excellent yields with outstanding diastereoselectivity. The synthetic utility of this protocol was further demonstrated through productive transformations of the resulting spirolactam products, highlighting their potential as valuable intermediates for complex molecule synthesis.
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