dc.creator | Flach, Andrew Louis | |
dc.date.accessioned | 2020-08-22T20:52:37Z | |
dc.date.available | 2019-08-28 | |
dc.date.issued | 2017-08-28 | |
dc.identifier.uri | https://etd.library.vanderbilt.edu/etd-08252017-154856 | |
dc.identifier.uri | http://hdl.handle.net/1803/14013 | |
dc.description.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. | |
dc.format.mimetype | application/pdf | |
dc.subject | Iodolactones | |
dc.subject | Halolactonization | |
dc.subject | Lactones | |
dc.subject | Iodolactonization | |
dc.subject | Counterions | |
dc.title | Investigation of Counterion Effects in an Organocatalyzed Iodolactonization and Discovery of an Organocatalyzed Iodolactonization to Give 7-Membered Lactones | |
dc.type | thesis | |
dc.contributor.committeeMember | Nathan D. Schley, Ph.D. | |
dc.contributor.committeeMember | Steven D. Townsend, Ph.D. | |
dc.type.material | text | |
thesis.degree.name | MS | |
thesis.degree.level | thesis | |
thesis.degree.discipline | Chemistry | |
thesis.degree.grantor | Vanderbilt University | |
local.embargo.terms | 2019-08-28 | |
local.embargo.lift | 2019-08-28 | |
dc.contributor.committeeChair | Jeffrey N. Johnston, Ph.D. | |