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Updated: May 29, 2026

Efficient Construction of Drug-like Bispirocyclic Scaffolds Via Organocatalytic Cycloadditions of α-Imino γ-Lactones and Alkylidene Pyrazolones
Published on: February 7, 2019
Catalytic intermolecular hetero-dehydro-Diels-Alder cycloadditions: regio- and diasteroselective synthesis of
Jesús Manuel Fernández-García1, Manuel Á Fernández-Rodríguez, Enrique Aguilar
1Instituto Universitario de Química Organometálica Enrique Moles, Universidad de Oviedo, C/Julián Clavería, 8, 33006 Oviedo, Asturias, Spain.
Abstract:
A novel catalyzed intermolecular heterodehydro-Diels-Alder reaction between push-pull 1,3-dien-5-ynes and aldimines or silylaldimines is reported. The sequence is promoted both by gold(I) or silver(I) catalysts and leads to the diastereo- and regioselective formation of 5,6-dihydropyridin-2-ones.
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Conformation
The simplest example of a diene is 1,3-butadiene, an acyclic conjugated π system. At room temperature, the molecule exists as a mixture of s-cis and s-trans conformers by virtue of rotation around the carbon–carbon single bond. Although the s-trans isomer is more stable, the...

