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Correction: Regioselective synthesis of aza-saccharins via anionic [1,4] Fries-type rearrangement of aryl sulfonimidoyl fluorides

Mario Leypold*a, Lorenzo Polia, Max Earla, Okky D. Putrab, Karolina Kwapiena, Richard J. Lewisa, John J. Murphya, Marta Passamontia, Lena M. von Sydowa, Victor Spellingc, Ioannis Asproudisb, Malvika Sardanac, Claudia Gattid, Hikaru Sekia, Thomas Lemaitrea, Radvile Juskaitea, Ranganath Gopalakrishnana, Stuart J. Francisa, Cristina Gardellia, Per-Ola Norrbye and Werngard Czechtizkya
aMedicinal Chemistry, Research and Early Development, Respiratory and Immunology, BioPharmaceuticals R&D AstraZeneca, Pepparedsleden 1, 43183 Mölndal, Sweden. E-mail: mario.leypold@astrazeneca.com
bEarly Product Development and Manufacturing, Pharmaceutical Sciences, R&D AstraZeneca, Pepparedsleden 1, 43183 Mölndal, Sweden
cEarly Chemical Development, Pharmaceutical Sciences, R&D AstraZeneca, Pepparedsleden 1, 43183 Mölndal, Sweden
dEarly Chemical Development, Pharmaceutical Sciences, R&D AstraZeneca, Macclesfield SK10 2NA, UK
ePredictive Science, Digital and Automation, Pharmaceutical Sciences, R&D AstraZeneca, Pepparedsleden 1, 43183 Mölndal, Sweden

Received 14th May 2026 , Accepted 14th May 2026

First published on 27th May 2026


Abstract

Correction for ‘Regioselective synthesis of aza-saccharins via anionic [1,4] Fries-type rearrangement of aryl sulfonimidoyl fluorides’ by Mario Leypold et al., Chem. Sci., 2026, https://doi.org/10.1039/d6sc00432f.


The authors regret that acetylated sulfonimidoyl fluoride 7a was depicted incorrectly in Scheme 4A of the original article and that “acyl chloride” in the caption of Scheme 4 should read “acetyl chloride”. The corrected version of Scheme 4 is displayed below. Acetylated sulfonimidoyl fluoride 7a is formed directly from the aryl sulfonimidoyl fluoridate anion 6a upon trapping with acetyl chloride and should therefore feature a tert-butyl ester group in the ortho-position relative to the sulfonimidoyl fluoride moiety, rather than the methyl ester group shown in the original article. The corrected structure is consistent with that provided in the original version of the supplementary information (SI).
image file: d6sc90113a-s4.tif
Scheme 4 Summary of mechanistic experiments for the formation of aza-saccharins. Reaction conditions: sulfonimidoyl fluoride (1 equiv.), KHMDS (2.00 equiv.), THF, −78 °C; 2-aminopyridine (2c, 1.20 equiv.), 4-Me-6-Ph-pyrimidine-2-amine (2b, 1.20 equiv.) or acetyl chloride (6.00 equiv.), THF, −78 °C, 22 °C, 15 min. aReaction profile for the KPA of unlabeled sulfonimidoyl fluoride 1a was computed at the M06-2X/def2-TZVP level of theory with implicit solvent model (COSMO) for the treatment of THF. The relative Gibbs free energies ΔΔG195 are calculated at 195 K. Values correspond to isolated yields. Displacement ellipsoids are drawn at the 30% and 50% probability level. Hydrogen atoms and minor parts are omitted for clarity.

The Royal Society of Chemistry apologises for these errors and any consequent inconvenience to authors and readers.


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