Synthesis of Enantioenriched Primarytert-Butanesulfonimidamidesvia Imination-Hydrazinolysis ofN′-tert-Butanesulfinyl Amidines

Thefirst synthesis of primarytert-butanesulfonimida-mides with high enantiopurity was realized by imination (or imination/N-functionalization) of enantioenrichedN '-tert-butanesulfinyl ami-dines, followed by hydrazinolysis.N '-Sulfinyl amidines served asimination precursors during copper-catalyzed sulfonyl nitrene transferor iodonitrene-based NH transfer. Further transformations allowedaccess to primarytert-butanesulfonimidamides with diverse substitu-tions on the nitrogen of S=N.

Automated summary

The first synthesis of primary tert-butanesulfonimides with high enantiopurity was achieved by imination of enantioenriched N'-tert-butanesulfinyl amidines, followed by hydrazinolysis. N'-Sulfinyl amidines served as imination precursors during copper-catalyzed sulfonyl nitrene transfer or iodonitrene-based NH transfer. Further transformations allowed the introduction of diverse substituents on the nitrogen of S=N.