A study of intermolecular and intramolecular Horner-Wadsworth-Emmons olefination of substituted 5- (Diethoxyphosphoryl)-N-acylpiperidin-4-ones /

by 1975- Ollinger, Christian G.

Ollinger, Christian G.: A Study of Intermolecular and Intramolecular Horner Wadsworth-Emmons Olefination of Substituted 5-(Diethoxyphosphoryl)-Nacylpiperidin-4-ones. (Under the direction of Dr. Daniel L. Comins) 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)-N-acylpiperidin-4-one allowed cyclization to occur thereby providing a bicyclic enone. A Study of Intermolecular and Intramolecular Horner-Wadsworth-Emmons Olefination of Substituted 5-(Diethoxyphosphoryl)-N-acylpiperidin-4-ones by Christian G. Ollinger A thesis submitted to the Graduate Faculty of North Carolina State University in partial fulfillment of the requirements for the degree of Master of Science Department of Chemistry Raleigh, North Carolina 2000