Preparation of Aliphatic Ketones
through a Ruthenium-Catalyzed Tandem
Cross-Metathesis/Allylic Alcohol
Isomerization
David Finnegan,Benjamin A. Seigal, andMarc L. Snapper*
Department of Chemistry, Merkert Chemistry Center, Boston College,
2609 Beacon Street, Chestnut Hill, Massachusetts 02467
marc.snapper@bc.edu
Received April 14, 2006
Abstract:
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.
