Date of Award

Spring 5-2016

Degree Type

Honors College Thesis


Chemistry and Biochemistry

First Advisor

Douglas Masterson

Advisor Department

Chemistry and Biochemistry


L-Proline is an amino acid widely used in pharmaceutical and biotechnological research due to its catalytic activity and biological relevance. L-Proline has been recognized and utilized as an organocatalyst, which allows cleaner, more sustainable reactions. However, one issue with L-proline is its low solubility in organic systems, limiting its reactivity and efficiency, especially when considering industrial research. Two reactions that utilize L-Proline are the Michael and Aldol but require 100 mol% of L-Proline and 30 mol% of L-Proline, respectively. This research will focus on the synthesis of an analogue of L-Proline utilizing inexpensive, commercially available reagents. A variety of organic reactions are used to generate the analogue whose structure is adapted for better solubility. The analogue is known to the Masterson research group and involves a multi-step synthesis, so efforts to improve the current synthetic strategy were made to maximize the efficiency of the production for the analogue. The current method has shown to be the most efficient pathway allowing maximum production at each step. Future goals for the project will include using organic reactions, including Aldol and Michael, to analyze the solubility and reactivity of the analogue and compare with studies performed with L-Proline.