Open Access. Powered by Scholars. Published by Universities.®
Articles 1 - 1 of 1
Full-Text Articles in Chemistry
Leveraging The 1,3-Azadiene-Anhydride Reaction For The Synthesis Of Functionalized Piperidines Bearing Up To Five Contiguous Stereocenters, Jorge Garcia, Jane Eichwald, Jayme Zesiger, Timothy K. Beng
Leveraging The 1,3-Azadiene-Anhydride Reaction For The Synthesis Of Functionalized Piperidines Bearing Up To Five Contiguous Stereocenters, Jorge Garcia, Jane Eichwald, Jayme Zesiger, Timothy K. Beng
Student Published Works
A modular and scalable strategy, which remodels 3-methylglutaric anhydride to 2-oxopiperidines bearing at least three contiguous stereocenters is described. The approach relies on the chemoselective and stereocontrolled annulation of 1,3-azadienes with the anhydride component. The resulting acid-tethered allylic 2-oxopiperidines are then engaged in several selective fragment growth processes, including catalytic denitrative alkenylation, halolactonization, and Vilsmeier–Haack functionalization.