Investigation of Counterion Effects in an Organocatalyzed Iodolactonization and Discovery of an Organocatalyzed Iodolactonization to Give 7-Membered Lactones

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 asymm...

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Main Author:	Flach, Andrew Louis
Other Authors:	Nathan D. Schley, Ph.D.
Format:	Others
Language:	en
Published:	VANDERBILT 2017
Subjects:	Chemistry
Online Access:	http://etd.library.vanderbilt.edu/available/etd-08252017-154856/

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spelling	ndltd-VANDERBILT-oai-VANDERBILTETD-etd-08252017-1548562017-08-29T05:21:59Z Investigation of Counterion Effects in an Organocatalyzed Iodolactonization and Discovery of an Organocatalyzed Iodolactonization to Give 7-Membered Lactones Flach, Andrew Louis Chemistry 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 Î´-iodolactones via modulation of the catalyst salt counterion. It further details the discovery of an enantioselective iodolactonization towards the much more challenging Îµ-iodolactones reliant upon an organocatalyst and a new oxidant system, along with subsequent reaction optimization, limited mechanistic investigation, and preliminary substrate scope. Nathan D. Schley, Ph.D. Steven D. Townsend, Ph.D. Jeffrey N. Johnston, Ph.D. VANDERBILT 2017-08-28 text application/pdf http://etd.library.vanderbilt.edu/available/etd-08252017-154856/ http://etd.library.vanderbilt.edu/available/etd-08252017-154856/ en restricted I hereby certify that, if appropriate, I have obtained and attached hereto a written permission statement from the owner(s) of each third party copyrighted matter to be included in my thesis, dissertation, or project report, allowing distribution as specified below. I certify that the version I submitted is the same as that approved by my advisory committee. I hereby grant to Vanderbilt University or its agents the non-exclusive license to archive and make accessible, under the conditions specified below, my thesis, dissertation, or project report in whole or in part in all forms of media, now or hereafter known. I retain all other ownership rights to the copyright of the thesis, dissertation or project report. I also retain the right to use in future works (such as articles or books) all or part of this thesis, dissertation, or project report.
collection	NDLTD
language	en
format	Others
sources	NDLTD
topic	Chemistry
spellingShingle	Chemistry Flach, Andrew Louis Investigation of Counterion Effects in an Organocatalyzed Iodolactonization and Discovery of an Organocatalyzed Iodolactonization to Give 7-Membered Lactones
description	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 Î´-iodolactones via modulation of the catalyst salt counterion. It further details the discovery of an enantioselective iodolactonization towards the much more challenging Îµ-iodolactones reliant upon an organocatalyst and a new oxidant system, along with subsequent reaction optimization, limited mechanistic investigation, and preliminary substrate scope.
author2	Nathan D. Schley, Ph.D.
author_facet	Nathan D. Schley, Ph.D. Flach, Andrew Louis
author	Flach, Andrew Louis
author_sort	Flach, Andrew Louis
title	Investigation of Counterion Effects in an Organocatalyzed Iodolactonization and Discovery of an Organocatalyzed Iodolactonization to Give 7-Membered Lactones
title_short	Investigation of Counterion Effects in an Organocatalyzed Iodolactonization and Discovery of an Organocatalyzed Iodolactonization to Give 7-Membered Lactones
title_full	Investigation of Counterion Effects in an Organocatalyzed Iodolactonization and Discovery of an Organocatalyzed Iodolactonization to Give 7-Membered Lactones
title_fullStr	Investigation of Counterion Effects in an Organocatalyzed Iodolactonization and Discovery of an Organocatalyzed Iodolactonization to Give 7-Membered Lactones
title_full_unstemmed	Investigation of Counterion Effects in an Organocatalyzed Iodolactonization and Discovery of an Organocatalyzed Iodolactonization to Give 7-Membered Lactones
title_sort	investigation of counterion effects in an organocatalyzed iodolactonization and discovery of an organocatalyzed iodolactonization to give 7-membered lactones
publisher	VANDERBILT
publishDate	2017
url	http://etd.library.vanderbilt.edu/available/etd-08252017-154856/
work_keys_str_mv	AT flachandrewlouis investigationofcounterioneffectsinanorganocatalyzediodolactonizationanddiscoveryofanorganocatalyzediodolactonizationtogive7memberedlactones
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Investigation of Counterion Effects in an Organocatalyzed Iodolactonization and Discovery of an Organocatalyzed Iodolactonization to Give 7-Membered Lactones

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