Enantiospecific Synthesis of Aniline-Derived Sulfonimidamides

Enantiospecific Synthesis of Aniline-Derived Sulfonimidamides

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 experim...

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Bibliographic Details
Published in:Organic letters Vol. 25; no. 30; pp. 5666 - 5670
Main Authors: Liang, Dong-Dong, Lional, Natassa, Scheepmaker, Bas, Subramaniam, Muthusamy, Li, Guanna, Miloserdov, Fedor M., Zuilhof, Han
Format: Journal Article
Language:English
Published: United States American Chemical Society 04-08-2023
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Letter
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Summary: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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ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.3c02132