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Synthesis 2010(21): 3649-3656
DOI: 10.1055/s-0030-1258227
DOI: 10.1055/s-0030-1258227
PAPER
© Georg Thieme Verlag
Stuttgart ˙ New York
Trapping the π-Allylpalladium Intermediate from Fulvene-Derived Azabicyclic Olefin with Soft Nucleophiles
Weitere Informationen
Publikationsverlauf
Received
17 June 2010
Publikationsdatum:
25. August 2010 (online)


Abstract
A facile method for the synthesis of a new class of disubstituted alkylidenecyclopentenes has been introduced. The methodology involves the palladium-catalyzed ring opening of pentafulvene-derived bicyclic hydrazines with phenols and active methylene compounds, furnishing 1,4-disubstituted alkylidenecyclopentenes in good yield. The utility of multiple points of functionalization was effectively demonstrated by the synthesis of a substituted cyclopentanone and 2-hydrazinofulvene.
Key words
azabicyclic olefin - palladium - soft nucleophile - alkylidenecyclopentene - substituted cyclopentanone - 2-hydrazinofulvene