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Title

Gold-Catalyzed [4C+2C] Cycloadditions of Allenedienes, including an Enantioselective Version with New Phosphoramidite-Based Catalysts: Mechanistic Aspects of the Divergence between [4C+3C] and [4C+2C] Pathways

AuthorsAlonso, Isaac; Trillo, Beatriz; López, Fernando; Montserrat, Sergi; Ujaque, Gregori; Castedo, Luis; Lledós, Agustí; Mascareñas, José L.
Issue Date21-Aug-2009
PublisherAmerican Chemical Society
CitationJ. Am. Chem. Soc., 2009, 131 (36), pp 13020–13030
AbstractGold(I) complexes featuring electron acceptor ligands such as phosphites and phosphoramidites catalyze the [4C+2C] intramolecular cycloaddition of allenedienes. The reaction is chemo- and stereoselective, and provides trans-fused bicyclic cycloadducts in good yields. Moreover, using novel chiral phosphoramidite-based gold catalysts it is possible to perform the reaction with excellent enantioselectivity. Experimental and theoretical data dismiss a cationic mechanism involving intermediate II and suggest that the formation of the [4C+2C] cycloadducts might arise from a 1,2-alkyl migration (ring contraction) in a cycloheptenyl Au-carbene intermediate (IV), itself arising from a [4C+3C] concerted cycloaddition of the allenediene. Therefore, these [4C+2C] allenediene cycloadditions and the previously reported [4C+3C] counterparts most likely share such cycloaddition step, differing in the final 1,2-migration step.
Publisher version (URL)http://pubs.acs.org/doi/full/10.1021/ja905415r
URIhttp://hdl.handle.net/10261/16838
DOIDOI: 10.1021/ja905415r
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