Enantiospecific Synthesis of Aniline-Derived Sulfonimidamides.

ABSTRACT: Reaction of sulfonimidoyl fluorides with anilines and Ca(NTf₂)₂ results in the formation of chiral sulfonimidamides. The reaction proceeds with inversion of the stereocenter at a sulfur atom. Enantiospecificity of the reaction was observed for all studied non-heterocyclic anilines. Combined experimental and computational mechanistic studies highlight chelate-type coordination of the sulfonimidoyl group to Ca(NTf₂)₂ and the formation of a S_N2-like transition state, in which leaving F^- coordinates with the Ca²⁺ ion.

SUBMITTER: Liang DD 

PROVIDER: S-EPMC10407922 | biostudies-literature | 2023 Aug

REPOSITORIES: biostudies-literature