Combining biocatalytic oxyfunctionalisation and organocatalytic aldol reaction to access chiral β-hydroxy ketones
This study explores a chemoenzymatic cascade to synthesise chiral β-hydroxy ketones by integrating the selective oxyfunctionalisation capabilities of peroxygenases with the carbon-carbon bond-forming progress of organocatalysts. Initial results with simple organocatalysts demonstrated poor performan...
| Autores: | , , , , , , , , |
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| Formato: | artículo |
| Estado: | Versión publicada |
| Fecha de publicación: | 2024 |
| País: | España |
| Recursos: | Consejo Superior de Investigaciones Científicas (CSIC) |
| Repositorio: | DIGITAL.CSIC. Repositorio Institucional del CSIC |
| OAI Identifier: | oai:digital.csic.es:10261/389594 |
| Acesso em linha: | http://hdl.handle.net/10261/389594 https://api.elsevier.com/content/abstract/scopus_id/85203185643 |
| Access Level: | acceso abierto |
| Palavra-chave: | Asymmetric aldol reaction Chemoenzymatic cascade Organocatalysis Oxyfunctionalisation Peroxygenase |
| Resumo: | This study explores a chemoenzymatic cascade to synthesise chiral β-hydroxy ketones by integrating the selective oxyfunctionalisation capabilities of peroxygenases with the carbon-carbon bond-forming progress of organocatalysts. Initial results with simple organocatalysts demonstrated poor performance due to mutual inactivation of the biocatalyst and organocatalyst. However, the use of more complex prolinamide derivatives improved the reaction efficiency and enantioselectivity, enabling a one-pot, one-step synthesis process. This methodology was further optimised to produce high yields of enantiomerically pure aldol products and was shown to be extendable to other substituted toluenes and aldol donors. |
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