Radical-mediated cyclopropane fragmentation approach to pyrrolidine and piperidine synthesis

ORGN 500

R. Stephen Andrews, andrewrs@jmu.edu and Kevin P. C. Minbiole, minbiokp@jmu.edu. Department of Chemistry, James Madison University, Harrisonburg, VA 22807
A method for formation of nitrogen-containing five- and six-membered heterocycles has been proposed and preliminary research has been conducted. A β-azidocyclopropanol substrate has been prepared by a two-step synthesis, and cyclization has been attempted using various oxidants and solvents. The heterocycle has not been synthesized to date, but proof of concept has been accomplished by creating a β-azidoethylketone. Preliminary research on an α-azidocyclopropanol substrate has been conducted with the intention to cyclize into the corresponding pyrrolidine.