Preparation of Aliphatic Ketones through a Ruthenium-Catalyzed Tandem Cross-Metathesis/Allylic Alcohol Isomerization
David Finnegan, Benjamin A. Seigal and Marc L. Snapper*
*Department of Chemistry, Merkert Chemistry Center, Boston College, 2609 Beacon Street, Chestnut Hill, Massachusetts 02467, Email: marc.snapperbc.edu
D. Finnegan, B. A. Seigal, M. L. Snapper, Org. Lett., 2006, 8, 2603-2606.
DOI: 10.1021/ol060918g (free Supporting Information)
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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 in a single-flask process that provides highly functionalized, ketone-containing products.
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A. A. Scholte, M. H. An, M. L. Snapper, Org. Lett., 2006, 8, 4759-4762.