Asymmetric Synthesis of Complex Heterocycles from Simple Cyclopropanes

University Of North Carolina At Chapel Hill, Chapel Hill NC

Investigators

Abstract

This project seeks to develop donor-acceptor cyclopropanes as simple, but broadly useful building blocks for a range of formal [3+2] cycloaddition reactions. Intercepting Lewis acid activated malonyl cyclopropanes with aldehydes, ketenes, cyclic imines, nitriles, and azo compounds will be studied to deliver tetrahydrofurans, cyclic enol ethers, bicyclic pyrrolidines, pyrrolines, and pyrazolidines, respectively. The project could lead to the rapid access to key substructures of naturally occurring biologically active compounds like the cladiellin diterpenes. With this award, the Organic and Macromolecular Chemistry Program is supporting the research of Professor Jeffrey Johnson of the Department of Chemistry at the University of North Carolina at Chapel Hill. Professor Johnson's research efforts are broadly in the area of chemical synthesis. The chemistry to be developed under the aegis of this grant is projected to positively impact the efficiency with which structurally interesting heterocyclic structures may be prepared in the laboratory. Such substructures are ubiquitous in biologically active natural products and medicinal agents.