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- Title
Palladium Catalyzed Ring-Opening of Diazabicylic Olefins with 4-Halo-1,3-Dicarbonyl Compounds: Accessing 3(2 H)-Furanone-Appended Cyclopentenes.
- Authors
Omanakuttan, Vishnu K.; Valsan, Alisha; Hopf, Henning; John, Jubi
- Abstract
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.
- Subjects
ALKENES; CYCLOPENTENES; FURANONES; NUCLEOPHILIC substitution reactions; INTRAMOLECULAR forces
- Publication
Organics, 2023, Vol 4, Issue 1, p70
- ISSN
2673-401X
- Publication type
Article
- DOI
10.3390/org4010006