Date of Award

Spring 2016

Document Type


Terms of Use

© 2016 Raundi E. Quevedo. All rights reserved. This work is freely available courtesy of the author. It may only be used for non-commercial, educational, and research purposes. For all other uses, including reproduction and distribution, please contact the copyright holder.

Degree Name

Bachelor of Arts


Chemistry & Biochemistry Department

First Advisor

Robert S. Paley


Broadly, the goal of this research was to observe the scope of the molecules we could make, how effective the syntheses were, and what the broader outcomes were. One objective of this research was to observe how oxazolidinoyl iron tricarbonyl diene scaffolds could be used for the diastereoselective synthesis of molecules. To determine the substrate scope, we wanted to manipulate the group functionalization at the R1 and R2 side chain. We were able to incorporate the desired aldehyde both at the R1 and the R2 position, although subsequent manipulation was only successful at the R1 side chain. In addition to the aldehyde, we observed the successful incorporation of alcohol (protected and de-protected), ester, amide, vinyl and many other functional groups. Another objective of this research was to determine how effective the production of these molecules were, which involved looking at reaction yields, but most importantly, the diastereoselectivity of complexation and nucleophilic addition reactions. The yields for the Stille and complexation reactions, when the chiral auxiliary was the Evans oxazolidinone, were higher than those seen in the sulfoxide series (70-99% versus 55- 75%). To observe what affected the complexation diastereomeric ratios, we wanted to manipulate the selective synthesis of the diene unit by modifying the size of the R1 and R2 side chains. In the first chapter of this thesis, the iron complexation diastereoselectivities were shown to increase as the size of the R2 side chain increased. This corroborates the assumptions we made when the crystal structure for the oxazolidinoyl iron tricarbonyl diene system was resolved: it seems that in order to avoid non-bonding interactions between the R2 side chain and the oxazolidinone isopropyl group, the R2 side chain is distorted out of the diene's plane, which restricts its available conformations and thus enhances the complexation facial bias. All nucleophilic addition reactions on the oxazolidinoyl iron tricarbonyl diene complexes were perfect (100:0). The last objective of this research, and just like in any research, is to observe what we can do with this chemistry. Although several attempts were made on producing macrocyclic rings through Diels Alder reactions, none were successful. Despite this, we were able to determine a few viable synthetic routes to natural structural motifs.

Included in

Chemistry Commons