Open Access Senior Honors Thesis
Reductive cyclization via McMurry coupling is a common way to form pyrrolizidine rings. In this work we investigate the titanium-catalyzed McMurry coupling reaction leading to a pyrrolizidine alkaloid using density functional methods. Specifically, we compare the relative energies of all possible pinacolate intermediates at the UB3LYP/6-31G level of theory. The most stable intermediate is found to be the one resulting from C-O bond insertion in the ester group. The McMurry product is not predicted to form.
Livingston, Andrew Jozef, "A Density Functional Study of the Relative Stability of Intermediates in a McMurry Coupling Reaction" (2009). Senior Honors Theses. 226.