Date of Award

6-2020

Document Type

Open Access

Degree Name

Bachelor of Science

Department

Chemistry

First Advisor

James C. Adrian Jr.

Keywords

Reformatsky, beta-Lactam, gama-Lactam, Amino acid, Cathinone, Cyclization

Abstract

DUPONT, DYLAN. An Alternative Synthetic Pathway to γ-Lactam Compounds

Through the Application of Novel Reformatsky-Type Chemistry. Department

of Chemistry, June 2020

ADVISOR: James C. Adrian Jr. Ph.D.

It is the intent of the present report to relate the results of our attempt to elucidate and optimize a novel preparation of γ-lactam compounds. To achieve this end, it is proposed that the use of novel Reformatsky-type chemistry may provide a viable means. Generally, it has herein been validated that employment of α-amino ketones in traditional Reformatsky chemistry will form the traditional Reformatsky ester-adduct, and that this adduct is capable of spontaneously undergoing an intramolecular cyclization event that yields the desired γ-lactam moiety. The main hurdle in this chemical pathway is an energetic one, as the cyclization event has showed itself to be slightly less spontaneous than predicted. However, this obstacle can be overcome by altering the solvent identity as to increase the heating capacity of the system.

The present study was hindered by inefficacies in the preparations of ketone starting materials, all of which performed with markedly less fidelity than was purported by the literature. Therefore, improvements to the curation of starting materials will be necessary. Barring necessary amendments to the preparation of starting materials, the presently proposed Reformatsky-type chemistry appears to have great potential as a cogent and useful addition to the repertoire of synthetic strategies.

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