Document Type

Poster Presentation

Symposium Date

2011

Abstract

Trimethylenemethane (TMM) cycloaddition is a palladium(0)-catalyzed process by which five-membered carbon rings are formed. This process, though very useful, results in the loss of a reactive functional group, making further synthetic steps more difficult. In order to maintain the functional group, a new, highly-functionalized TMM cycloaddition was attempted with an epoxide precursor rather than the typical acetoxy group. This precursor, trimethyl(2-oxiranyl-2-propenyl)silane, was successfully synthesized in three steps from propargyl alcohol. The epoxide was then used in a palladium(0)-catalyzed TMM cycloaddition to result in the desired cyclopentane molecule, which retained the useful oxygen and trimethylsilyl group.

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