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Journal of Undergraduate Research

Keywords

microwave promoted iminyl, radical cyclization, biologically active compounds

College

Life Sciences

Department

Chemistry and Biochemistry

Abstract

Pyrrolidines and their derivatives are found in many biologically active compounds, such as Lipitor and Atorvastatin, which possess a wide variety of remarkable pharmaceutical properties. Therefore, the efficient synthesis of functionalized pyrrolidines is of great value to organic chemists. Multiple attempts have been made to synthesize compounds containing pyrrolidine ring systems. Walton 1 utilized radical cyclization, via microwave heating, to transform Ophenyl oximes with terminal alkenes to dihydropyrroles, compounds closely related to pyrrolidines. Similarly, Sammis 2 proposed a method involving radical cyclizations of azidederived aminyl radicals onto silyl enol ethers. Unfortunately, the method proposed by Sammis requires highly toxic and explosive reagents. The synthetic route proposed by Walton could in principle allow for an effective synthesis of important pyrrolidine ring systems, but to date no one has explored this application. Furthermore, Walton’s synthesis involves H atom trapping, which prevents access to highly functionalized compounds that could be obtained by trapping with other atoms.

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