An Amination-Cyclization Cascade Reaction for Iminosugar Synthesis Using Minimal Protecting Groups.

The development of a one-step amination-cyclization cascade reaction for the synthesis of N-substituted iminosugars from iodo-pentoses and hexoses is reported. This novel methodology allows for the stereoselective conversion of easily accessible iodo-aldoses and iodo-ketoses into iminosugars in a single step, in highly efficient yields (63-95%), and in aqueous media. Furthermore, the use of functionalized amines allows for the synthesis of N-functionalized iminosugars without additional steps. To illustrate this methodology, a number of biologically important iminosugars were prepared, including 1-deoxynojirimycin, (3 S ,4 R ,5 S ,6 R )-azepane-3,4,5,6-tetraol, and N-functionalized 1-deoxymannojirimycins.