Preparation of Aliphatic Ketones through a Ruthenium-Catalyzed Tandem Cross-Metathesis/Allylic Alcohol Isomerization

Grubbs' 2nd generation and Hoveyda−Grubbs' ruthenium alkylidenes are shown to be effective catalysts for cross-metatheses of allylic alcohols with cyclic and acyclic olefins, as well as isomerization of the resulting allylic alcohols to alkyl ketones. The net result of this new tandem meth...

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Veröffentlicht in:Organic letters 2006-06, Vol.8 (12), p.2603-2606
Hauptverfasser: Finnegan, David, Seigal, Benjamin A, Snapper, Marc L
Format: Artikel
Sprache:eng
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Zusammenfassung:Grubbs' 2nd generation and Hoveyda−Grubbs' ruthenium alkylidenes are shown to be effective catalysts for cross-metatheses of allylic alcohols with cyclic and acyclic olefins, as well as isomerization of the resulting allylic alcohols to alkyl ketones. The net result of this new tandem methodology is a single-flask process that provides highly functionalized, ketone-containing products from simple allylic alcohol precursors.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol060918g