A Modular Approach to Cyclopropanols through Carboxylate and Aldehyde-Derived Substrates

Overview

Cyclopropanes are important motifs found in natural products, commercial insecticides, and pharmaceutical compounds. However, their synthesis often relies on concerted reactions that limit modular control over substitution, with existing modular approaches frequently requiring toxic reagents or stoichiometric amounts of metal. This project investigates whether cyclopropanes, particularly cyclopropanols, could be assembled in a modular manner starting from carboxylate-derived substrates under base-metal conditions. It was hypothesized that integrating established carbene-generation strategies could enable modular cyclopropanol formation from simple building blocks. Initial experiments with dichloromethane and a carboxylate substrate under reductive iron and nickel catalyzed systems produced cyclopropanes in low yield, which improved with optimization of ligand, substrate, and additional reaction conditions. Following up on this hit, reaction conditions were systematically screened by varying catalysts, ligands, substrates, reagent equivalents, and temperature across multiple trials, with controls omitting key components. Introduction of a third bromo-benzoate reaction component enabled modular control with substituents. Removing dichloromethane from this tricomponent system resulted in enol ether formation, suggesting a step-wise pathway for cyclopropane formation. While the exact mechanism remains unconfirmed, this study demonstrates a modular tri-component assembly pathway for cyclopropane formation from carboxylates. Future work will focus on mechanistic studies, expanding substrate scope, and exploring synthetic applications in diverse scaffolds.

Competition history

• CSEF 2026 Chemistry (Senior Division) · Entry S-05-06

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