Synthesis of Sulfur-Stereogenic Sulfoximines via Co(III)/Chiral Carboxylic Acid-Catalyzed Enantioselective C-H Amidation

Sulfoximines bearing stereogenic sulfur atoms are ubiquitous motifs in pharmaceuticals, agricultural chemicals, and bioactive compounds. Herein, we report the synthesis of sulfur-stereogenic sulfoximines via Co(III)/chiral carboxylic acid-catalyzed enantioselective C-H amidation. A broad range of cyclic and acyclic sulfur-stereogenic sulfoximines were isolated in good yields and enantioselectivities (up to an 86% yield and 1.5:98.5 er). The acyclic amidation products can be reduced to potential N,S-chiral sulfoxide ligands, which could be further transformed into recyclable chiral auxiliaries in the Pd-catalyzed diastereoselective C(sp(3))-H activation of aliphatic carboxylic acids.

Automated summary

In this study, we report the synthesis of sulfur-stereogenic sulfoximines through Co(III)/chiral carboxylic acid-catalyzed reaction. The synthetic yields and enantioselectivities are high, and the products can be further transformed into recyclable chiral auxiliaries.