Leveraging the 1, 3-azadiene-anhydride reaction for the synthesis of functionalized piperidines bearing up to five contiguous stereocenters. Issue 1 (20th December 2021)

• Record Type: Journal Article
• Authors: Garcia, Jorge; Eichwald, Jane; Zesiger, Jayme; Beng, Timothy K.
• Is Part Of: RSC advances. Volume 12:Issue 1(2022)
• Page Start: 309
• Page End: 318
• Publication Date: 2021-12-20
• Subjects: Chemistry -- Periodicals; 540.5
• DOI: 10.1039/d1ra07390g
• Languages: English
• ISSNs: 2046-2069

Abstract

Abstract : A modular and scalable strategy, which converts 3-methylglutaric anhydride to 2-oxopiperidines bearing at least three contiguous stereocenters is described. 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.