Pyridine-Hydrazone Ligands in Asymmetric Palladium-Catalyzed 1,4- and 1,6-Additions of Arylboronic Acids to Cyclic (Di)enones
Catalysts generated by combinations of Pd(TFA)2 and enantiomerically pure pyridine-hydrazone ligands have been applied to the 1,4-addition of arylboronic acids to β-substituted cyclic enones, building all-carbon quaternary stereocenters in high yields and enantioselectivities (up to 93% ee). The dev...
| Autores: | , , , , , , |
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| Formato: | artículo |
| Estado: | Versión aceptada para publicación |
| Fecha de publicación: | 2019 |
| País: | España |
| Recursos: | Universidad de Sevilla (US) |
| Repositorio: | idUS. Depósito de Investigación de la Universidad de Sevilla |
| OAI Identifier: | oai:idus.us.es:11441/140540 |
| Acesso em linha: | https://hdl.handle.net/11441/140540 https://doi.org/10.1002/adsc.201801021 |
| Access Level: | acceso abierto |
| Palavra-chave: | Arylboronic acids Asymmetric Catalysis Hydrazones N Ligands Palladium |
| Resumo: | Catalysts generated by combinations of Pd(TFA)2 and enantiomerically pure pyridine-hydrazone ligands have been applied to the 1,4-addition of arylboronic acids to β-substituted cyclic enones, building all-carbon quaternary stereocenters in high yields and enantioselectivities (up to 93% ee). The developed methodology allows the efficient introduction of ortho-substituted aryl groups in β-position of cyclopentanone cores, giving scaffolds present in a broad range of biologically active natural products. These Pd(II)-complexes served also as catalysts in the 1,6-addition of arylboronic acids to cyclic dienones, affording complete regioselectivities, moderate yields and good enantioselectivities (up to 80% ee). |
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