Date Approved

2009

Degree Type

Open Access Senior Honors Thesis

Department

Chemistry

Abstract

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.

Included in

Chemistry Commons

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