Development of a Novel Epoxide-Containing Trimethylenemethane Precursor for Palladium-Catalyzed Cycloadditions

Pd(0)-catalyzed trimethylenemethane (TMM) cycloaddition reactions have been used extensively to generate disubstituted 5-membered rings with high levels of regioselectivity, chemoselectivity, and stereoselectivity. We aim to improve upon existing methodologies by introducing an epoxide into the TMM precursor, which should yield more highly functionalized products. A three step synthesis of a TMM precursor has been achieved in 20% overall yield. Efforts are underway to determine the reactivity of this precursor in Pd(0)-catalyzed cycloaddition reactions with substituted alkenes