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Updated: Jul 21, 2025

Preparation of Enantiopure Non-Activated Aziridines and Synthesis of Biemamide B, D, and epiallo-Isomuscarine
Published on: June 13, 2022
Enantiospecific Synthesis of Aniline-Derived Sulfonimidamides
Dong-Dong Liang1,2, Natassa Lional1, Bas Scheepmaker1
1Laboratory of Organic Chemistry, Wageningen University, Stippeneng 4, 6708 WE Wageningen, Netherlands.
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 SN2-like transition state, in which leaving F- coordinates with the Ca2+ ion.
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