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Lewis acid-catalyzed [2π+2σ] cycloaddition of dihydropyridines with bicyclobutanes.
Chem Commun (Camb)
January 2025
Organisch-Chemisches Institut, Universität Münster, Corrensstraße 40, 48149 Münster, Germany.
Herein we report a simple BF-catalyzed cycloaddition of dihydropyridines with bicyclobutanes for the expedient synthesis of novel three-dimensional azacycle-fused bicyclo[2.1.1]hexane scaffolds.
View Article and Find Full Text PDFDynamic Kinetic Activation of Aziridines Enables Radical-Polar Crossover (4 + 3) Cycloaddition with 1,3-Dienes.
J Am Chem Soc
January 2025
State Key Laboratory of Applied Organic Chemistry & College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou 730000, China.
The cycloaddition of aziridines with unsaturated compounds is a valuable method for synthesizing nitrogen heterocycles. However, this process is predominantly substrate-controlled, posing significant challenges in regulating the regioselectivity of the C-N bond cleavage. In this study, we report a nickel-catalyzed dynamic kinetic activation strategy that enables catalyst-controlled activation of aziridines.
View Article and Find Full Text PDFFrom Pseudocyclic to Macrocyclic Ionophores: Strategies toward the Synthesis of Cyclic Monensin Derivatives.
J Org Chem
January 2025
Department of Medical Chemistry, Faculty of Chemistry, Adam Mickiewicz University, Uniwersytetu Poznańskiego 8, 61-614 Poznań, Poland.
There has been a long search for a simple preparation of new cyclic analogues of ionophore antibiotics. We report a simple and general synthesis of three new cyclic derivatives of polyether ionophore, monensin A (MON). The application of the Huisgen 1,3-dipolar cycloaddition of azides and terminal alkynes to macrocyclization results in a concise, synthetic route to monensin lacton or lactam in only 4 steps.
View Article and Find Full Text PDFDiastereoselective Construction of Bridged Azabicyclo[3.2.1]octane via Copper-Catalyzed Formal [4 + 3] Cycloaddition.
J Org Chem
January 2025
Hubei Key Laboratory of Natural Medicinal Chemistry and Resource Evaluation, School of Pharmacy, Huazhong University of Science and Technology, 13 Hangkong Road, Wuhan, Hubei 430030, People's Republic of China.
A novel copper-catalyzed formal diastereoselective [4 + 3] cycloaddition of 2-arylaziridines and 2-substituted cyclopentadiene was developed. This transformation provided an efficient protocol for the assembly of a highly strained bridged azabicyclo[3.2.
View Article and Find Full Text PDFAsymmetric Total Syntheses of Sarglamides A, C, and E.
J Org Chem
January 2025
State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou, 730000 Gansu, P. R. China.
The asymmetric total syntheses of sarglamides A, C, and E in concise and protecting group free fashion is disclosed. Key steps involve an -selective Diels-Alder reaction to construct the bicyclo[2.2.
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