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Title page for ETD etd-08252017-154856

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
  • Iodolactones
  • Halolactonization
  • Lactones
  • Iodolactonization
  • Counterions
Date of Defense 2017-08-25
Availability restricted

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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