Sulfonimidamides
Given the lack of commercially available racemic sulfonimidamides, chemists generated a list totaling 117 diverse, synthetically-feasible sulfonimidamides. These included aryl, benzylic, allylic, alkyl, alkenyl, and alkynyl sulfonimidamides with various halide substitutions, heteroatom containing rings, and substitution patterns.
Publications
van Dijk, L.; Haas, B. C.; Lim, N.; Clagg, K.; Dotson, J. J.; Treacy, S. M.; Piechowicz, K. A.; Roytman, V. A.; Zhang, H.; Toste, F. D.; Miller, S. J.; Gosselin, F.; Sigman, M. S. "Data Science-Enabled Palladium-Catalyzed Enantioselective Aryl-Carbonylation of Sulfonimidamides." J. Am. Chem. Soc. 2023, 145, 20959–20967. https://doi.org/10.1021/jacs.3c06674
Haas, B. C.; Lim, N.-K.; Jermaks, J.; Gaster, E.; Guo, M. C.; Malig, T. C.; Werth, J.; Zhang, H.; Toste, F. D.; Gosselin, F.; Miller, S. J.; Sigman, M. S. Enantioselective Sulfonimidamide Acylation via a Cinchona Alkaloid-Catalyzed Desymmetrization: Scope, Data Science, and Mechanistic Investigation. J. Am. Chem. Soc. 2024, 146, 8536–8546. DOI: 10.1021/jacs.4c00374