Synthesis of Enantioenriched Primary tert-Butanesulfonimidamides via Imination-Hydrazinolysis of N'-tert-Butanesulfinyl Amidines.

Abstract

The first synthesis of primary tert-butanesulfonimidamides with high enantiopurity was realized by imination (or imination/N-functionalization) 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 access to primary tert-butanesulfonimidamides with diverse substitutions on the nitrogen of S═N.