Synthesis
DOI: 10.1055/a-2705-4564
Paper

Structure-Reactivity Relationships of Anomeric Amide Reagents in Nitrogen Deletion

Julia L Driscoll
1   Department of Chemistry, University of Chicago, Chicago, United States
,
Megan Morales
1   Department of Chemistry, University of Chicago, Chicago, United States
,
Carys E Obertone
1   Department of Chemistry, University of Chicago, Chicago, United States
,
Bumsu Park
1   Department of Chemistry, University of Chicago, Chicago, United States
,
Rubén Miguélez
1   Department of Chemistry, University of Chicago, Chicago, United States
,
1   Department of Chemistry, University of Chicago, Chicago, United States
› Author Affiliations

Supported by: Division of Chemistry CHE-2235826
Supported by: Division of Graduate Education DGE: 2140001
Supported by: Agencia Estatal de Investigación PID2019-107469RB-I00
Preview

N-(benzyloxy)-N-(pivaloyloxy)benzamides, a class of anomeric amide reagents, have enabled nitrogen deletion of secondary amines as well as deamination and deaminative functionalization of primary amines in a single step. While the application of these reagents has been expanding, current use is limited by the substrate limitations of existing anomeric amides. This report details the design and synthesis of novel anomeric amide derivatives with improved reaction kinetics, one of which demonstrates improved deletion yields in some instances. These studies shed light on the stereoelectronic effects governing the reactivity of anomeric amides within the context of nitrogen-deletion reactions.



Publication History

Received: 18 August 2025

Accepted after revision: 02 September 2025

Accepted Manuscript online:
19 September 2025

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