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Title

Gold-Catalyzed [4C+3C] Intramolecular Cycloaddition of Allenedienes: Synthetic Potential and Mechanistic Implications

AuthorsTrillo, Beatriz; López, Fernando; Montserrat, Sergi; Ujaque, Gregori; Castedo, Luis; Lledós, Agustí; Mascareñas, José L.
KeywordsAllenes
Carbocycles
Cycloaddition
Density functional calculations
Gold
Homogeneous catalysis
Issue Date19-Feb-2009
PublisherWiley-VCH
CitationA European Journal Chemistry - A European Journal Volume 15 Issue 14, Pages 3336 -
AbstractEfficient at room temperature: The Au complex generated in situ from [(IPr)AuCl] and AgSbF6 promotes the [4C+3C] intramolecular cycloaddition of allenes and dienes at room temperature, and in a particularly efficient and versatile manner. A DFT study on dimethylallenyl precursors agreed with the formation and cycloaddition of a metal-allyl cation intermediate, and points to the 1,2-hydride shift as the key rate-limiting step.
Publisher version (URL)http://www3.interscience.wiley.com/journal/122210085/abstract?CRETRY=1&SRETRY=0
URIhttp://hdl.handle.net/10261/16841
DOI10.1002/chem.200900164
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