College Honors Program

Title

The Synthesis of β-lactams via Copper Catalysis

Date of Creation

5-31-2023

Document Type

Campus Access Only

Department

Chemistry

First Advisor

André K. Isaacs

Abstract

Ketenimines are synthetic intermediates that are highly reactive with various nucleophiles. Our research group forms ketenimines through “click chemistry.” In this process, an alkyne reacts with tosyl azide in a copper catalyzed reaction to form a 1,4-disubstituted 1,2,3-triazole, which decomposes into the reactive ketenimine intermediate. The ketenimine then reacts with added nucleophiles to form nitrogen heterocycles.

We utilize this ketenimine intermediate in a spontaneous intramolecular reaction with a tethered ethynyl ether nucleophile in order to synthesize β-lactam precursors. β-lactams are a vital structural component of many antibiotics, making their synthesis very important in light of the public health crisis of increasing bacterial resistance to treatment. We have generated a variety of substrates that can successfully participate in the copper catalyzed reaction in order to showcase the utility of our method. Our future work will involve conversion of these β-lactam precursors into fully functionalized β-lactams.

Comments

Reader: Christine Hagan

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