Covering: 2006 to 2018 The application of the 6π-azaelectrocyclization of azatrienes as a key strategy for the synthesis of natural products, their analogs and related bioactive or biomedically-relevant compounds (from 2006 to date) is comprehensively reviewed. Details about reaction optimization studies, relevant reaction mechanisms and conditions are also discussed.
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Insights into the mechanism, selectivity, and substituent effects in the Diels-Alder reaction of azatrienes with electron-rich dienophiles: An MEDT study.
J Mol Graph Model
November 2024
Laboratory of Spectroscopy, Molecular Modeling, Materials, Nanomaterials, Water and Environment, LS3MN2E/CERNE2D, Faculty of Sciences, Mohammed V University in Rabat, Morocco. Electronic address:
The reactivity and mechanistic intricacies of azatrienes in Diels-Alder reactions have been relatively unexplored despite their intriguing potential applications. In this study, we employ Molecular Electron Density Theory to theoretically investigate the hetero-Diels-Alder reaction involving azatrienes with ethyl vinyl ether and allenyl methyl ether. Analysis of Conceptual Density Functional Theory, energetic profiles, and the topological characteristics is conducted to elucidate the reactions.
View Article and Find Full Text PDFCopper-Catalyzed Diastereo-, Enantio-, and ()-Selective Aminoallylation of Ketones through Reductive Couplings of Azatrienes for the Synthesis of Allylic 1,2-Amino Tertiary Alcohols.
J Am Chem Soc
July 2024
Department of Chemistry, Duke University, Durham, North Carolina 27708, United States.
We introduce a method for the ()-selective aminoallylation of a range of ketones to prepare allylic 1,2-amino tertiary alcohols with excellent diastereo- and enantioselectivity. Copper-catalyzed reductive couplings of 2-azatrienes with aryl/alkyl and dialkyl ketones proceed with Ph-BPE as the supporting ligand, generating -amino alcohols with >98% ()-selectivity under mild conditions. The utility of the products is highlighted through several transformations, including those that leverage the ()-allylic amine moiety for diastereoselective reactions of the alkene.
View Article and Find Full Text PDFSynthesis of 1-Azatriene Complexes of Tungsten: Metal-Promoted Ring-Opening of Dihydropyridine.
Organometallics
May 2024
Department of Chemistry, University of Virginia, Charlottesville, Virginia 22904, United States.
For nearly a century, chemists have explored how transition-metal complexes can affect the physical and chemical properties of linear conjugated polyenes and heteropolyenes. While much has been written about higher hapticity complexes (η-η), less is known about the chemistry of their η analogues. Herein, we describe a general method for synthesizing 5,6-η-(1-azatriene) tungsten complexes via a 6π-azaelectrocyclic dihydropyridine ring-opening that is promoted by the π-basic nature of {WTp(NO)(PMe)}.
View Article and Find Full Text PDFScalable Total Synthesis of Acremolactone B.
Angew Chem Int Ed Engl
July 2024
College of Chemistry and Henan Institute of Advanced Technology, Zhengzhou University, Zhengzhou, 450001, China.
Acremolactone B is a pyridine-containing azaphilone-type polyketide. The first total synthesis of this molecule was achieved on a gram scale, based on an aza-6π electrocyclization-aromatization strategy for construction of the tetra-substituted pyridine ring. A bicyclic intermediate was expeditiously prepared by using [2+2] photocycloaddition and chemoselective Baeyer-Villiger oxidation, which was further elaborated to a densely substituted aza-triene.
View Article and Find Full Text PDFOne-Pot Knoevenagel/Imination/6π-Azaelectrocyclization Sequence for the Synthesis of Disubstituted Nicotinonitriles.
J Org Chem
July 2023
Department of Chemistry, National Taiwan Normal University, No. 88, Sec. 4, Ting-Zhou Road, Taipei 11677, Taiwan, R.O.C.
We report on a copper-catalyzed three-component reaction for the synthesis of disubstituted nicotinonitriles using 3-bromopropenals, benzoylacetonitriles, and ammonium acetate (NHOAc). The Knoevenagel-type condensation of 3-bromopropenals with benzoylacetonitriles gives δ-bromo-2,4-dienones that contain strategically placed functional groups that react with the ammonia generated to give the corresponding azatrienes. These azatrienes can then be transformed into trisubstituted pyridines under the reaction conditions via a reaction sequence involving 6π-azaelectrocyclization and aromatization.
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