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The palladium-catalyzed cycloisomerization of acyclic bisdienes to cyclized enedienes defines a novel strategy for the stereoselective cyclization of certain unsymmetric bisdiene substrates to form functionalized five- and six-membered rings. The full details of our investigation into this novel cycloisomerization, including our observations on substrate requirements, stereoselectivity, the influence of the catalyst precursor, and some mechanistic insights drawn from deuterium labeling studies, are discussed.

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1997 ring closure reactions ring closure reactions O 0130 -065Catalytic Palladium-Mediated Bisdiene Carbocyclizations: Bisdiene to Enediene Cycloisomerizations.-Several examples are investigated in the Pd-catalyzed cycloisomerization of acyclic bisdienes to cyclized products defining a novel strategy for this stereoselective cyclization. Functionalized fiveand six-membered rings are generally formed in high yield and with high diastereoselectivity. The cyclization establishes the trans relative stereochemistry between the unsaturated side chains on the newly formed ring. In terms of labelling studies some mechanistic insights are discussed in order to assess the influence of the catalytic precursor, ligand and solvent. -(TAKACS, J. M.; CLEMENT, F.; ZHU, J.; CHANDRAMOULI, S. V.; GONG, X.; J. Am. Chem.