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.
