Issue 1, 2022

Leveraging the 1,3-azadiene-anhydride reaction for the synthesis of functionalized piperidines bearing up to five contiguous stereocenters

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.

Graphical abstract: Leveraging the 1,3-azadiene-anhydride reaction for the synthesis of functionalized piperidines bearing up to five contiguous stereocenters

Supplementary files

Article information

Article type
Paper
Submitted
04 Oct 2021
Accepted
10 Dec 2021
First published
20 Dec 2021
This article is Open Access
Creative Commons BY-NC license

RSC Adv., 2022,12, 309-318

Leveraging the 1,3-azadiene-anhydride reaction for the synthesis of functionalized piperidines bearing up to five contiguous stereocenters

J. Garcia, J. Eichwald, J. Zesiger and T. K. Beng, RSC Adv., 2022, 12, 309 DOI: 10.1039/D1RA07390G

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