Synfacts 2008(3): 0283-0283  
DOI: 10.1055/s-2008-1042691
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Catalytic Nucleophilic Ring Closure ofπ-Allylpalladium Intermediates

Contributor(s): Mark Lautens, Praew Thansandote
R. Shintani*, S. Park, T. Hayashi*
Kyoto University, Japan
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Publication History

Publication Date:
21 February 2008 (online)


The authors describe the development of a palladium-catalyzed intermolecular ­cycloaddition that involves a nucleophliic ring closure to the central carbon of a π-allylpalladium intermediate. Spiro[2,4]heptanes are obtained in good yields and moderate diastereoselectivities using small phosphite ligands. If bulky phosphine ligands are used, a selective [4+2] cycloaddition occurs, leading to exo-methylene cyclohexane products.