Morita-Baylis-Hillman Cyclizations of Arene-Ruthenium-Functionalized Acrylamides

Morita-Baylis-Hillman Cyclizations of Arene-Ruthenium-Functionalized Acrylamides

Enticed by metalation with a {CpRuII} fragment, N‐benzyl and N‐phenethyl acrylamides participate in phosphine‐promoted spirocyclizations even though they are normally unreactive in Morita–Baylis–Hillman (MBH)‐type transformations. A ruthenium–arene cation serves as the electrophilic reaction partner...

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Veröffentlicht in:Angewandte Chemie International Edition 2007-01, Vol.46 (16), p.2887-2890
Hauptverfasser: Pigge, F. Christopher, Dhanya, R., Hoefgen, Erik R.
Format: Artikel
Sprache:eng
Schlagworte:
arene ligands
dearomatization
nitrogen heterocycles
ruthenium
spiro compounds
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Zusammenfassung:Enticed by metalation with a {CpRuII} fragment, N‐benzyl and N‐phenethyl acrylamides participate in phosphine‐promoted spirocyclizations even though they are normally unreactive in Morita–Baylis–Hillman (MBH)‐type transformations. A ruthenium–arene cation serves as the electrophilic reaction partner for an in situ generated enolate ion in this organometallic variation of the MBH reaction.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.200605045