Type of Document Master's Thesis Author Flach, Andrew Louis URN etd-08252017-154856 Title Investigation of Counterion Effects in an Organocatalyzed Iodolactonization and Discovery of an Organocatalyzed Iodolactonization to Give 7-Membered Lactones Degree Master of Science Department Chemistry Advisory Committee
Advisor Name Title Jeffrey N. Johnston, Ph.D. Committee Chair Nathan D. Schley, Ph.D. Committee Member Steven D. Townsend, Ph.D. Committee Member Keywords
Date of Defense 2017-08-25 Availability restricted Abstract
Iodolactonization is a venerable chemical reaction with considerable utility in the synthesis of organic compounds. More recently, enantioselective methods reliant upon organocatalysts have been developed. This work details the investigation into a previously developed organocatalyst-mediated asymmetric iodolactonization towards δ-iodolactones via modulation of the catalyst salt counterion. It further details the discovery of an enantioselective iodolactonization towards the much more challenging ε-iodolactones reliant upon an organocatalyst and a new oxidant system, along with subsequent reaction optimization, limited mechanistic investigation, and preliminary substrate scope.
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