We report a tBuOK-promoted synthesis of 1,3-dihydro-2H-pyrrol-2-one and 4-methylenepyrrolidin-2-one systems via Conia-ene like intramolecular cyclization. The method features extremely short reaction times (5 min) and mild reaction conditions (rt), enabling the trapping of a propargyl unit by an amide enolate. An intriguing anionic chain mechanism is at work, which can trigger the isomerization of an exo-alkene giving access to the otherwise elusive endo-product.
Base-promoted Conia-ene cyclization of propargyl amides / Cerveri, A.; Vettori, M.; Serafino, A.; Maestri, G.. - In: ORGANIC & BIOMOLECULAR CHEMISTRY. - ISSN 1477-0520. - 21:36(2023), pp. 7311-7315. [10.1039/d3ob01107k]
Base-promoted Conia-ene cyclization of propargyl amides
Cerveri A.;Vettori M.;Serafino A.;Maestri G.
2023-01-01
Abstract
We report a tBuOK-promoted synthesis of 1,3-dihydro-2H-pyrrol-2-one and 4-methylenepyrrolidin-2-one systems via Conia-ene like intramolecular cyclization. The method features extremely short reaction times (5 min) and mild reaction conditions (rt), enabling the trapping of a propargyl unit by an amide enolate. An intriguing anionic chain mechanism is at work, which can trigger the isomerization of an exo-alkene giving access to the otherwise elusive endo-product.I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
