Palladium Catalyzed Ring-Opening of Diazabicylic Olefins with 4-Halo-1,3-Dicarbonyl Compounds: Accessing 3(2H)-Furanone-Appended Cyclopentenes

Autor: Vishnu K. Omanakuttan, Alisha Valsan, Henning Hopf, Jubi John
Jazyk: angličtina
Rok vydání: 2023
Předmět:
Zdroj: Organics, Vol 4, Iss 1, Pp 70-85 (2023)
Druh dokumentu: article
ISSN: 2673-401X
DOI: 10.3390/org4010006
Popis: We have realized a Pd-catalyzed ring-opening of diazabicyclic olefins with 4-halo-1,3-dicarbonyl compounds. This reaction resulted in the formation of 3(2H)-furanone-appended hydrazino cyclopentenes. The reaction proceeds via the formation of a π-allylpalladium intermediate which is attacked by the active methylene species, and an intramolecular nucleophilic substitution in the 4-halo-1,3-dicarbonyl moiety furnishes the 3(2H)-furanone-substituted cyclopentene. We could extend this methodology to cyclopropane-appended spirotricyclic olefin for synthesizing 3(2H)-furanone-substituted spiro[2.4]hept-5-ene.
Databáze: Directory of Open Access Journals
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