Artículo
Pyridine-Hydrazone Ligands in Asymmetric Palladium-Catalyzed 1,4- and 1,6-Additions of Arylboronic Acids to Cyclic (Di)enones
Autor/es | de Gracia Retamosa, María
Álvarez Casao, Yolanda Matador Martínez, Esteban Gómez, Ángela Monge Fernández, David Fernández Fernández, Rosario Fátima Lassaletta, José M. |
Departamento | Universidad de Sevilla. Departamento de Química orgánica |
Fecha de publicación | 2019 |
Fecha de depósito | 2022-12-15 |
Publicado en |
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Resumen | 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 ... 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). |
Agencias financiadoras | Ministerio de Asuntos Económicos y Transformación Digital (MINECO). España Junta de Andalucía |
Identificador del proyecto | CTQ2016-76908-C2-2-P
CTQ2016-76908-C2-1-P 2012/FQM1078 |
Cita | de Gracia Retamosa, M., Álvarez Casao, Y., Matador Martínez, E., Gómez, Á., Monge Fernández, D., Fernández Fernández, R.F. y Lassaletta, J.M. (2019). Pyridine-Hydrazone Ligands in Asymmetric Palladium-Catalyzed 1,4- and 1,6-Additions of Arylboronic Acids to Cyclic (Di)enones. Advanced Synthesis and Catalysis, 361 (1), 176-184. https://doi.org/10.1002/adsc.201801021. |
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