Pd(0)-Catalyzed TMM Cycloadditions with Epoxide-Modified Precursors: A New Approach to 5-Membered Ring Synthesis
Level of Education of Students Involved
Undergraduate
Faculty Sponsor
Dr. Kevin Jantzi
College
College of Arts & Sciences (CAS)
Discipline(s)
Chemistry, Organic Chemistry, Chemical Synthesis
ORCID Identifier(s)
0009-0006-8220-4083
Presentation Type
Poster Presentation
Symposium Date
Spring 4-24-2025
Abstract
Pd0-catalyzed trimethylenemethane (TMM) cycloaddition reactions have been used extensively to generate substituted 5-membered rings with high levels of regioselectivity, chemoselectivity, and stereoselectivity. These rings have many practical applications, such as polymer and pharmaceutical molecule synthesis. We aim to improve upon existing methodologies by introducing an epoxide functional group into the TMM precursor molecule, which should yield more highly functionalized products. A three-step synthesis of a TMM precursor has been achieved in 20% overall yield, quantified by structure and mass analysis at each step. Efforts are underway to determine the reactivity of this precursor in Pd0-catalyzed cycloaddition reactions with α,β-unsaturated carbonyl compounds.
Recommended Citation
Brezina, Nolan; Parrillo, Johana; and Jantzi, Kevin, "Pd(0)-Catalyzed TMM Cycloadditions with Epoxide-Modified Precursors: A New Approach to 5-Membered Ring Synthesis" (2025). Symposium on Undergraduate Research and Creative Expression (SOURCE). 1392.
https://scholar.valpo.edu/cus/1392
Biographical Information about Author(s)
Nolan and Johana are both students working through chemistry majors at Valpo. Both became interested in organic synthesis after learning chemistry at Valpo and plan to pursue science in the future.