Synthesis of Chiral Sulfilimines via Copper-Catalyzed Enantiospecific Arylation of Sulfenamides

Abstract

Chiral sulfilimines represent a type of chiral S(IV) compound that is versatile as pharmacophores and chiral building blocks for chiral S(VI) compounds. Herein, we report an efficient method of preparing chiral sulfilimines (up to 90% yield and up to 96% enantiomeric excess) from commercially available diaryliodonium salts and prochiral sulfenamides. The reaction was enlarged to the gram scale for the preparation of chiral sulfilimines and allowed for the derivatization of chiral sulfoximines and sulfondiimines with complete retention of stereochemistry.