An inverse-electron-demand aza-Diels-Alder reaction between 4,4-dicyano-2-methylenebut-3-enoates and 1,3,5-triazinanes under catalyst-free and additive-free conditions was developed, which provided a highly convenient and straightforward method to construct a series of polyfunctionalized tetrahydropyridines in high yields. This strategy features numerous advantages, including high efficiency, good functional group tolerance, broad substrate scope, and environmentally friendly conditions.
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http://dx.doi.org/10.1039/d3ob00511a | DOI Listing |
Beilstein J Org Chem
December 2024
Departamento de Química Orgánica y Química Inorgánica, Instituto de Investigación Química "Andrés M. del Río" (IQAR), Universidad de Alcalá (IRYCIS), 28805 Madrid, Spain.
Asymmetric cycloaddition is a straightforward strategy which enables the synthesis of structurally distinct cyclic derivatives which are difficult to access by other methodologies, using an efficient and atom-economical path from simple precursors. In recent years several asymmetric catalytic cyclization strategies have been accomplished for the construction of -heterocycles using various catalytic systems such as chiral metal catalysts, chiral Lewis acids or chiral organocatalysts. This review presents an overview of the recent advances in enantioselective cyclization reactions of 1-azadienes catalyzed by non-covalent organocatalysts.
View Article and Find Full Text PDFJACS Au
June 2024
Department of Chemistry, Indian Institute of Science Education & Research Bhopal, Bhopal, Madhya Pradesh 462066, India.
Reported herein are the bench stable (24)-diazohexa-2,4-dienals (diazodienals) and their unprecedented polycyclization with aldimine and arylamines enabled by Rh(II)/Brønsted acid relay catalysis. This scalable and atom-economical reaction provides direct access to the biologically important azatricyclo[6.2.
View Article and Find Full Text PDFOrg Lett
September 2023
Pingyuan Laboratory, State Key Laboratory of Antiviral Drugs, School of Chemistry and Chemical Engineering, Henan Normal University, Xinxiang, Henan 453007, China.
A highly efficient asymmetric inverse-electron-demand aza-Diels-Alder reaction of β-trifluoromethyl α,β-unsaturated ketone with cyclic -sulfonyl ketimines catalyzed by ()-3,3'-I-BINOL-boron-complex was developed. A broad range of fused piperidine derivatives bearing stereogenic carbon containing CF motifs were prepared in high yields with excellent diastereo- and enantioselectivities (up to >20:1 dr, and >99% ee). This protocol had the characteristics of mild reaction conditions, high efficiency, and high stereoselectivity.
View Article and Find Full Text PDFACS Omega
June 2023
Central Laboratory, Chongqing University Fuling Hospital, Chongqing 408000, PR China.
The chemoselective annulation of aza--quinone methide generated by in situ -chloromethyl sulfonamide has been achieved with bifunctional acyclic olefin. This efficient approach provides access to the diastereoselective synthesis of functionalized tetrahydroquinoline derivatives containing indole scaffolds through the inverse-electron-demand aza-Diels-Alder reaction under mild reaction conditions with excellent results (up to 93% yield, > 20:1 dr). Moreover, this article realized the cyclization of α-halogeno hydrazone with electron-deficient alkene affording the tetrahydropyridazine derivatives, which had never been reported.
View Article and Find Full Text PDFOrg Biomol Chem
July 2023
School of Pharmacy, Zunyi Medical University, Zunyi 563000, China.
An inverse-electron-demand aza-Diels-Alder reaction between 4,4-dicyano-2-methylenebut-3-enoates and 1,3,5-triazinanes under catalyst-free and additive-free conditions was developed, which provided a highly convenient and straightforward method to construct a series of polyfunctionalized tetrahydropyridines in high yields. This strategy features numerous advantages, including high efficiency, good functional group tolerance, broad substrate scope, and environmentally friendly conditions.
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