Sulfonamides are used extensively in the agrochemical and medicinal chemistry industries. However, until recently the use of sulfoximines and sulfonimidamides as analogues has been limited. These attractive new functional groups offer favourable physicochemical properties and access new chemical and IP-space. Notably, the sulfoximine group has been seen in clinical drug candidates from Bayer and AstraZeneca.<br/>This presentation will cover our work in this field, developing operationally simple metal-free methods for the synthesis of NH-sulfoximines and NH-sulfonimidamides. A hypervalent iodine mediated (formal) nitrene transfer using simple ammonium salts as the source of nitrogen provides NH-sulfoximines directly from sulfoxides, with retention of any enantiomeric excess. Similarly, one-pot conversions of sulfides to sulfoximines, and sulfenamides to sulfonimidamides, is achieved with a remarkable chemoselective NH and O transfer. A new approach to the preparation of enantiopure sulfonimidamides by stereospecific reaction of stable, chiral sulfonimidoyl fluorides will also be presented. These reagents are suitable for reaction with neutral amines, including late-stage functionalisation.

Synthesis of sulfoximines and sulfonimidamides as chiral sulfonamide alternatives with attractive properties

ACS Fall 2020 Virtual Meeting

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