The Use of Chiral Dihydropyridones in the Development of Novel Synthetic Methodology

Amine cleavage;von Bruan;Heterocycles;Dihydropyridone

McCall, W. Stephen Jr. ; Dr. John Cavanagh, Committee Member,Dr. Christian Corey Melander, Committee Member,Dr. Daniel Comins, Committee Chair,Dr. Thomas Brent Gunnoe, Committee Member,Dr. Jon S Lindsey, Committee Member,McCall, W. Stephen Jr. ; Dr. John Cavanagh ; Committee Member ; Dr. Christian Corey Melander ; Committee Member ; Dr. Daniel Comins ; Committee Chair ; Dr. Thomas Brent Gunnoe ; Committee Member ; Dr. Jon S Lindsey ; Committee Member

University:North Carolina State University

关键词: Amine cleavage;    von Bruan;    Heterocycles;    Dihydropyridone;   

Others  :  https://repository.lib.ncsu.edu/bitstream/handle/1840.16/5440/etd.pdf?sequence=1&isAllowed=y

美国|英语

来源: null

【 摘 要 】

A chiral ligand was synthesized using an enantiopure dihydropyridone as starting material. The ligand was tested for efficacy in thediethyl zinc aldehyde addition reaction, giving poor chiral induction. The von Braun tertiary amine cleavage reaction was used to regio and stereoselectively ring open chiral piperidines with varying degrees of substitution. The mechanistic course of the reaction was investigated and postulated. A new silyl assisted (SivB) version of the von Braun reaction was discovered. This was utilized to open piperidines to give a terminal alkene as a useful synthetic handle remaining in the molecule.