Organocatalytic kinetic resolution of 1,5-dicarbonyl compounds through a retro-Michael reaction
The pharmaceutical chemical industry has long used kinetic resolution to obtain high-value compounds. Organocatalysis has recently been added to this strategy, allowing for the resolution of racemic mixtures with low catalyst loadings and mild reaction conditions. This research focuses on the kineti...
Saved in:
| Main Authors: | , , , |
|---|---|
| Format: | Article |
| Language: | English |
| Published: |
Beilstein-Institut
2025-03-01
|
| Series: | Beilstein Journal of Organic Chemistry |
| Subjects: | |
| Online Access: | https://doi.org/10.3762/bjoc.21.34 |
| Tags: |
Add Tag
No Tags, Be the first to tag this record!
|
| _version_ | 1849728734242799616 |
|---|---|
| author | James Guevara-Pulido Fernando González-Pérez José M. Andrés Rafael Pedrosa |
| author_facet | James Guevara-Pulido Fernando González-Pérez José M. Andrés Rafael Pedrosa |
| author_sort | James Guevara-Pulido |
| collection | DOAJ |
| description | The pharmaceutical chemical industry has long used kinetic resolution to obtain high-value compounds. Organocatalysis has recently been added to this strategy, allowing for the resolution of racemic mixtures with low catalyst loadings and mild reaction conditions. This research focuses on the kinetic resolution of 1,5-dicarbonyl compounds using a retro-Michael reaction, co-catalyzed at room temperature with 20 mol % of the Jørgensen–Hayashi catalyst and PNBA. The study highlights the importance of conducting the kinetic resolution at a concentration of approximately ten millimolar (mM) to prevent the Michael retro-Michael equilibrium from affecting the process. |
| format | Article |
| id | doaj-art-b8c9865f14414a2f8a7dcaec32cedbbf |
| institution | DOAJ |
| issn | 1860-5397 |
| language | English |
| publishDate | 2025-03-01 |
| publisher | Beilstein-Institut |
| record_format | Article |
| series | Beilstein Journal of Organic Chemistry |
| spelling | doaj-art-b8c9865f14414a2f8a7dcaec32cedbbf2025-08-20T03:09:28ZengBeilstein-InstitutBeilstein Journal of Organic Chemistry1860-53972025-03-0121147348210.3762/bjoc.21.341860-5397-21-34Organocatalytic kinetic resolution of 1,5-dicarbonyl compounds through a retro-Michael reactionJames Guevara-Pulido0Fernando González-Pérez1José M. Andrés2Rafael Pedrosa3Química Farmacéutica, Grupo Investigación en Química Aplicada INQA, Universidad El Bosque, Cra 7b Bis No 132 – 11, Bogotá, Colombia Instituto Universitario CINQUIMA y Departamento de Química Orgánica, Facultad de Ciencias, Universidad de Valladolid, Paseo Belén 7, 47011-Valladolid, Spain Instituto Universitario CINQUIMA y Departamento de Química Orgánica, Facultad de Ciencias, Universidad de Valladolid, Paseo Belén 7, 47011-Valladolid, Spain Instituto Universitario CINQUIMA y Departamento de Química Orgánica, Facultad de Ciencias, Universidad de Valladolid, Paseo Belén 7, 47011-Valladolid, Spain The pharmaceutical chemical industry has long used kinetic resolution to obtain high-value compounds. Organocatalysis has recently been added to this strategy, allowing for the resolution of racemic mixtures with low catalyst loadings and mild reaction conditions. This research focuses on the kinetic resolution of 1,5-dicarbonyl compounds using a retro-Michael reaction, co-catalyzed at room temperature with 20 mol % of the Jørgensen–Hayashi catalyst and PNBA. The study highlights the importance of conducting the kinetic resolution at a concentration of approximately ten millimolar (mM) to prevent the Michael retro-Michael equilibrium from affecting the process.https://doi.org/10.3762/bjoc.21.341,5-dicarbonylequilibriumkinetic resolutionorganocatalysisretro-michael |
| spellingShingle | James Guevara-Pulido Fernando González-Pérez José M. Andrés Rafael Pedrosa Organocatalytic kinetic resolution of 1,5-dicarbonyl compounds through a retro-Michael reaction Beilstein Journal of Organic Chemistry 1,5-dicarbonyl equilibrium kinetic resolution organocatalysis retro-michael |
| title | Organocatalytic kinetic resolution of 1,5-dicarbonyl compounds through a retro-Michael reaction |
| title_full | Organocatalytic kinetic resolution of 1,5-dicarbonyl compounds through a retro-Michael reaction |
| title_fullStr | Organocatalytic kinetic resolution of 1,5-dicarbonyl compounds through a retro-Michael reaction |
| title_full_unstemmed | Organocatalytic kinetic resolution of 1,5-dicarbonyl compounds through a retro-Michael reaction |
| title_short | Organocatalytic kinetic resolution of 1,5-dicarbonyl compounds through a retro-Michael reaction |
| title_sort | organocatalytic kinetic resolution of 1 5 dicarbonyl compounds through a retro michael reaction |
| topic | 1,5-dicarbonyl equilibrium kinetic resolution organocatalysis retro-michael |
| url | https://doi.org/10.3762/bjoc.21.34 |
| work_keys_str_mv | AT jamesguevarapulido organocatalytickineticresolutionof15dicarbonylcompoundsthrougharetromichaelreaction AT fernandogonzalezperez organocatalytickineticresolutionof15dicarbonylcompoundsthrougharetromichaelreaction AT josemandres organocatalytickineticresolutionof15dicarbonylcompoundsthrougharetromichaelreaction AT rafaelpedrosa organocatalytickineticresolutionof15dicarbonylcompoundsthrougharetromichaelreaction |