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.
Cassell, Samantha, "Highly Functionalized Pd(0)-Catalyzed Trimethylenemethane (TMM) Cycloadditions" (2011). Symposium on Undergraduate Research and Creative Expression (SOURCE). 76.