Enantiospecific Synthesis of Aniline-Derived Sulfonimidamides

Dong Dong Liang; Natassa Lional; Bas Scheepmaker; Muthusamy Subramaniam; Guanna Li; Fedor M. Miloserdov; Han Zuilhof

doi:10.1021/acs.orglett.3c02132

Enantiospecific Synthesis of Aniline-Derived Sulfonimidamides

Dong Dong Liang, Natassa Lional, Bas Scheepmaker, Muthusamy Subramaniam, Guanna Li, Fedor M. Miloserdov^*, Han Zuilhof^*

^*Corresponding author for this work

Research output: Contribution to journal › Article › Academic › peer-review

3 Citations (Scopus)

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.

Original language	English
Pages (from-to)	5666-5670
Number of pages	5
Journal	Organic Letters
Volume	25
Issue number	30
DOIs	https://doi.org/10.1021/acs.orglett.3c02132
Publication status	Published - 4 Aug 2023

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10.1021/acs.orglett.3c02132Licence: CC BY

https://edepot.wur.nl/637403Licence: CC BY

CCDC 2277657: Experimental Crystal Structure Determination
Liang, D. D. (Creator), Lional, N. (Creator), Scheepmaker, B. (Creator), Subramaniam, M. (Creator), Li, G. (Creator), Miloserdov, F. (Creator) & Zuilhof, H. (Creator), Wageningen University & Research, 28 Jun 2023
DOI: 10.5517/ccdc.csd.cc2gg2tv
Dataset
CCDC 2277656: Experimental Crystal Structure Determination
Liang, D. D. (Creator), Lional, N. (Creator), Scheepmaker, B. (Creator), Subramaniam, M. (Creator), Li, G. (Creator), Miloserdov, F. (Creator) & Zuilhof, H. (Creator), Wageningen University & Research, 28 Jun 2023
DOI: 10.5517/ccdc.csd.cc2gg2st
Dataset

Cite this

@article{1ad0945c5ed3413cb9643b9665aae0fb,

title = "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 SN2-like transition state, in which leaving F- coordinates with the Ca2+ ion.",

author = "Liang, {Dong Dong} and Natassa Lional and Bas Scheepmaker and Muthusamy Subramaniam and Guanna Li and Miloserdov, {Fedor M.} and Han Zuilhof",

year = "2023",

month = aug,

day = "4",

doi = "10.1021/acs.orglett.3c02132",

language = "English",

volume = "25",

pages = "5666--5670",

journal = "Organic Letters",

issn = "1523-7060",

publisher = "American Chemical Society",

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}

TY - JOUR

T1 - Enantiospecific Synthesis of Aniline-Derived Sulfonimidamides

AU - Liang, Dong Dong

AU - Lional, Natassa

AU - Scheepmaker, Bas

AU - Subramaniam, Muthusamy

AU - Li, Guanna

AU - Miloserdov, Fedor M.

AU - Zuilhof, Han

PY - 2023/8/4

Y1 - 2023/8/4

N2 - 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.

AB - 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.

U2 - 10.1021/acs.orglett.3c02132

DO - 10.1021/acs.orglett.3c02132

M3 - Article

C2 - 37490052

AN - SCOPUS:85166470745

SN - 1523-7060

VL - 25

SP - 5666

EP - 5670

JO - Organic Letters

JF - Organic Letters

IS - 30

ER -

Enantiospecific Synthesis of Aniline-Derived Sulfonimidamides

Abstract

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Datasets

CCDC 2277657: Experimental Crystal Structure Determination

CCDC 2277656: Experimental Crystal Structure Determination

Cite this