Paul earned his B.A. in Chemistry from Wheaton College (MA) in 2013. He is pursuing his Ph.D. in Organic Chemistry at Indiana University Bloomington, in the laboratories of Silas Cook. His research interest include the activation of alcohols under mild Lewis acid conditions to synthesize small heterocycles present in many biologically active small molecules, as well as the synthesis of photocaged drug compounds.
Small nitrogen containing heterocycles are ubiquitous in organic natural products, pharmaceuticals and biologically active small molecules. Synthesis of 5-membered pyrrolidine and indoline rings with defined stereochemistry adjacent to the nitrogen remain a challenge. We have developed mild conditions to activate alcohols for nucleophilic attack where the only stoichiometric byproduct of the reaction is water. Utilizing enantioenriched alcohols and nitrogen nucleophiles with an iron Lewis acid catalyst, we are able to synthesize stereodefined pyrrolidine and indoline rings in excellent yield and enantiospecificity. We are currently exploring applying this methodology to target molecules of biological interest as well as screening novel chiral indolines and pyrrolidines for biological activity.