Synthetic approaches and applications of sulfonimidates.

This review article explores the synthesis of the organosulfur(vi) species named sulfonimidates, focusing on their synthesis from sulfur(ii), sulfur(iv) and sulfur(vi) reagents, and investigates their recent resurgeance in interest as intermediates to access other important organosulfur compounds. Sulfonimidates have been utilized as precursors for polymers, sulfoximine and sulfonimidamide drug candidates and as alkyl transfer reagents.

General Method for the Asymmetric Synthesis of N-H Sulfoximines via C-S Bond Formation.

A versatile method for the synthesis of enantioenriched N-H sulfoximines is reported. The approach stems from the organomagnesium-mediated ring opening of novel cyclic sulfonimidate templates. The reactions proceed in high yield and with excellent stereofidelity with alkyl, aryl, and heteroaryl Grignard reagents.

Sulfonimidates: Useful Synthetic Intermediates for Sulfoximine Synthesis via C-S Bond Formation.

Medicinally relevant sulfoximines are accessed from C-S coupling of sulfonimidates and commercially available organomagnesium reagents. Sulfonimidates are conveniently synthesized by oxidative alkoxylation of readily available sulfinamides. This constitutes a general C-S coupling approach for the synthesis of sulfoximines.