Synthesis of aza-S(VI) motifs

Abstract

Sulfoximines and sulfonimidamides are of interest as design options for medicinal chemists. This article describes the development of methods for the synthesis of sulfoximines by metal-free NH-transfer to sulfoxides, and NH/O transfer to sulfides, using convenient sources of ammonia and hypervalent iodine reagents. Similarly, sulfonimidamides are prepared from sulfenamides. Methods for the preparation of enantioenriched sulfonimidoyl fluorides are also described, as are their stereospecific reactions with amines and Grignard reagents. This work was presented at the 29^th International Symposium on the Organic Chemistry of Sulfur (Guelph, July 2022).