Document Type
Article
Department or Administrative Unit
Chemistry
Publication Date
12-20-2021
Abstract
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.
Recommended Citation
Garcia, J., Eichwald, J., Zesiger, J., & Beng, T. K. (2022). Leveraging the 1,3-azadiene-anhydride reaction for the synthesis of functionalized piperidines bearing up to five contiguous stereocenters. RSC Advances, 12(1), 309–318. https://doi.org/10.1039/d1ra07390g
Journal
RSC Advances
Creative Commons License
This work is licensed under a Creative Commons Attribution-NonCommercial 4.0 International License
Rights
© 2022 The Author(s). Published by the Royal Society of Chemistry
Comments
This article was originally published Open Access in RSC Advances. The full-text article from the publisher can be found here.