A Study of Intermolecular and Intramolecular Horner-Wadsworth-Emmons Olefination of Substituted5-(Diethoxyphosphoryl)-N-acylpiperidin-4-ones

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Title: A Study of Intermolecular and Intramolecular Horner-Wadsworth-Emmons Olefination of Substituted5-(Diethoxyphosphoryl)-N-acylpiperidin-4-ones
Author: Ollinger, Christian G.
Advisors: Dr. Daniel L. Comins, Chair
Dr. Suzanne T. Purrington, Member
Dr. Binghe Wang, Member
Abstract: This research has focused on extending the utility of previously synthesized 5-iodo-2,3-dihydro-4-pyridones. The initial conversion involved introducing a phosphonate group by nickel-catalyzed cross-coupling with the vinyl iodide at the C-5 position. Using a Horner-Wadsworth-Emmons reaction, the phosphonate ester was then converted to various olefins in moderate to high yields. Having an aldehyde present on the substituted 5-(diethoxyphosphoryl)--acylpiperidin-4-one allowed cyclization to occur thereby providing a bicyclic enone.
Date: 2000-07-31
Degree: MS
Discipline: Chemistry
URI: http://www.lib.ncsu.edu/resolver/1840.16/1328


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