ArticleMolecules (Basel, Switzerland)2026
Synthesis of Spiro-Bridged 3,4-Dihydrocoumarins Through an Organocatalytic Cascade Sequence Diels-Alder/Nucleophilic Ring Closing.
Article in Molecules (Basel, Switzerland), 2026. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Not yet cited in PubMed.
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Abstract
3,4-dihydrocoumarins and spiro compounds constitute an important class of privileged frameworks present in a wide variety of natural and synthetic molecules with diverse applications. In this study, we developed an organocatalytic methodology for the construction of complex and diverse chiral spiro-bridged 3,4-dihydrocoumarins through a Diels-Alder/Nucleophilic ring-closing cascade via trienamine activation. The reaction proceeds efficiently with different trienamine precursors and a range of coumarin-3-carboxamides, which act as both dienophile and intramolecular nucleophile species. This process affords the desired products in good yields and with a high degree of stereocontrol. Furthermore, several transformations on the newly formed spiro-piperidone ring demonstrate the synthetic utility of the obtained compounds.
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