Synthesis of Chiral-at-Sulfur(VI) Sulfonimidamide Brønsted Acids.

Herein, we report an efficient and simple strategy to access diverse chiral-at-sulfur(VI) Brønsted acids. Sulfonimidoyl chlorides or fluorides react with sulfonamides with inversion of configuration, producing chiral-at-sulfur sulfonimidamides containing an acidic NH group. Similarly, reactions of sulfonimidoyl chlorides with corresponding sulfonimidamides give access to C2-symmetric chiral-at-sulfur Brønsted acids. Finally, attaching sulfonimidamides to a 1,1-bi-2-naphthol (BINOL)-derived phosphoryl chloride scaffold generates Brønsted acids combining sulfur-centered point chirality with BINOL axial chirality.