Cascade reactions: A modular assembly of azabicycles by using a cascade cyclization/Suzuki coupling/6π-electrocyclization of bromoenynamides is reported. The reaction offers a wide substituent scope on the bicyclic aminodiene products, which can be selectively oxidized as a general approach to aromatic azabicycles.
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http://dx.doi.org/10.1002/chem.201102880 | DOI Listing |
J Org Chem
November 2024
Jiangsu Key Laboratory of Drug Design and Optimization, Department of Medicinal Chemistry, School of Pharmacy, China Pharmaceutical University, Nanjing 210009, China.
Bicyclo[3.2.1]octane (BCO) skeleton widely exists in natural products and biologically active molecules, whereas the development of convenient approaches to construct this structure remains a challenge.
View Article and Find Full Text PDFJ Org Chem
September 2024
Key Lab of Colloid and Interface Chemistry, Ministry of Education, Institute of Theoretical Chemistry, School of Chemistry and Chemical Engineering, Shandong University, Jinan 250100, P. R. China.
Density functional theory calculations were conducted to refine our understanding at the molecular level of the synthesis of fused 1,2-dihydroquinolines through Rh- and acid-catalyzed skeleton-reorganizing coupling reactions of cycloheptatriene with amines. The results reveal that the reaction progresses via cascade catalysis, consisting of consecutive steps of Rh-catalyzed intermolecular coupling involving two Rh-Rh-Rh transformations with a maximum energy barrier of 27.1 kcal/mol, followed by acid-catalyzed intramolecular skeleton reorganization with a peak energy barrier of 23.
View Article and Find Full Text PDFOrg Lett
April 2024
Department of Chemical Sciences, Indian Institute of Science Education and Research Kolkata, Mohanpur 741246, West Bengal, India.
An electrocatalytic approach to access structurally significant azabicyclic scaffolds from -allyl enamine carboxylates is illustrated. This metal-free method functions exclusively with a catalytic amount of iodide, strategically employed to electrochemically generate a reactive hypervalent iodine species, which facilitates the cascade bicyclization processes with enhanced precision and efficiency. Excellent functional group compatibility was observed, enabling the synthesis of a series of azabicycle derivatives.
View Article and Find Full Text PDFChem Commun (Camb)
May 2021
Department of Chemistry, Purdue University, IN 47907, USA.
The first photoinduced synthesis of polyfunctionalized 3-aza[n.1.0]bicycles from readily available ene-ynamides and 2,6-lutidine N-oxide using an organic acridinium photocatalyst is reported.
View Article and Find Full Text PDFAcc Chem Res
May 2020
College of Chemistry and Molecular Sciences, Wuhan University, Wuhan 430072, China.
Optically active nitrogen-containing compounds have attracted substantial attention due to their ubiquity in the cores of natural products and bioactive molecules. Among the various synthetic approaches to nitrogenous frameworks, catalytic asymmetric 1,3-dipolar cycloadditions are one of the most attractive methods because of their powerful ability to rapidly construct various chiral -heterocycles. In particular, -metallated azomethine ylides, common and readily available 1,3-dipoles, have been extensively applied in dipolar cycloaddition reactions.
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