Novel cyclic sugar imines: carbohydrate mimics and easily elaborated scaffolds for aza-sugars.

Abstract

[reaction: see text] Representative simple or polyhydroxylated, pyrrolidine (e.g, DRAM) or piperidine (e.g., DNJ) imines not only are potential carbohydrate-processing enzyme inhibitors that may be formed as regioisomeric variants but also are scaffolds that may be rapidly elaborated to diversely functionalized aza-sugars through highly diastereoselective organometallic additions.