Article
An Efficient and Practical Method for the Enantioselective Synthesis of Tertiary Trifluoromethyl Carbinols
Author/s | Borrego Sánchez de la Cuesta, Lorenzo Gabriel
Recio Jiménez, Rocío Alcarranza Saucedo, Manuel Khiar, Noureddine Fernández Fernández, Inmaculada |
Department | Universidad de Sevilla. Departamento de Química Orgánica y Farmacéutica Universidad de Sevilla. Departamento de Farmacología |
Publication Date | 2018-03 |
Deposit Date | 2024-01-31 |
Published in |
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Awards | Premio Mensual Publicación Científica Destacada de la US. Facultad de Farmacia |
Abstract | An efficient sulfinamide/olefin based chiral ligand, MetSulfolefin, has been developed for the enantioselective rhodium-catalysed addition of aryl-boronic acids to trifluoromethyl ketones. This shelf-stable ligand is ... An efficient sulfinamide/olefin based chiral ligand, MetSulfolefin, has been developed for the enantioselective rhodium-catalysed addition of aryl-boronic acids to trifluoromethyl ketones. This shelf-stable ligand is insensitive to air, oxygen and moisture, and it is obtained in only two high yielding steps from cheap commercially available (R)-tert-butanesulfinamide. The new ligand tolerates the use of hindered boronic acids and leads to the formation of a series of chiral trifluoromethyl-substituted tertiary carbinols in high yields and excellent enantioselectivities (up to >99% ee). (Figure presented.). |
Funding agencies | Ministerio de Economía y Competitividad (MINECO). España Junta de Andalucía |
Project ID. | CTQ2016-78580-C2-2-R
CTQ2016-78580-C2-1-R 11-FQM-08046 |
Citation | Borrego Sánchez de la Cuesta, L.G., Recio Jiménez, R., Alcarranza Saucedo, M., Khiar, N. y Fernández Fernández, I. (2018). An Efficient and Practical Method for the Enantioselective Synthesis of Tertiary Trifluoromethyl Carbinols. Advanced Synthesis and Catalysis, 360 (6), 1273-1279. https://doi.org/10.1002/adsc.201701212. |
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