Article
Steric Tuning of Sulfinamide/Sulfoxides as Chiral Ligands with C1, Pseudo-meso, and Pseudo‑C2 Symmetries: Application in Rhodium(I)-Mediated Arylation
Author/s | Borrego Sánchez de la Cuesta, Lorenzo Gabriel
Recio Jiménez, Rocío Álvarez González, Eleuterio Sánchez Coronilla, Antonio Khiar, Noureddine Fernández Fernández, Inmaculada |
Department | Universidad de Sevilla. Departamento de Química Orgánica y Farmacéutica Universidad de Sevilla. Departamento de Química Física |
Publication Date | 2019-07-31 |
Deposit Date | 2020-01-23 |
Published in |
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Awards | Premio Anual Publicación Científica Destacada de la US. Facultad de Farmacia |
Abstract | A new family of sulfinamide/sulfoxide derivatives was synthesized as chiral bidentate ligands by stereoselective additions of methylsulfinyl carbanions to N-tert-butylsulfinylimines. The new ligands, with C1, pseudo-meso, ... A new family of sulfinamide/sulfoxide derivatives was synthesized as chiral bidentate ligands by stereoselective additions of methylsulfinyl carbanions to N-tert-butylsulfinylimines. The new ligands, with C1, pseudo-meso, and pseudo-C2 symmetries, were successfully assayed in Rh-catalyzed additions of arylboronic acids to activated ketones. The sterically dissymmetric C1 ligand (RS,SC,RS)-N-[1-(phenylsulfinyl)-3-methylbut-2-yl] tert-butylsulfinamide turned out to be the optimal one, allowing the 1,4-additions of diverse arylboronic acids, on different α,β-unsaturated cyclic ketones with high chemical yields and enantioselectivities up to >99% ee. |
Project ID. | CTQ2016-78580-C2-2R |
Citation | Borrego Sánchez de la Cuesta, L.G., Recio Jiménez, R., Álvarez González, E., Sánchez Coronilla, A., Khiar, N. y Fernández Fernández, I. (2019). Steric Tuning of Sulfinamide/Sulfoxides as Chiral Ligands with C1, Pseudo-meso, and Pseudo‑C2 Symmetries: Application in Rhodium(I)-Mediated Arylation. Organic Letters, 21 (16), 6513-6518. |
Files | Size | Format | View | Description |
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10.1021_acs.orglett.9b02405.pdf | 1007.Kb | [PDF] | View/ | Postprint |