Titanocene-Promoted Intermolecular Couplings of Epoxides with Nitriles. An Easy Access to β-Hydroxyketones

Fernández Mateos, Alfonso; Encinas Madrazo, Soledad; Herrero Teijón, Pablo; Rubio González, María Rosa

doi:10.1021/jo900479v

Título

Titanocene-Promoted Intermolecular Couplings of Epoxides with Nitriles. An Easy Access to β-Hydroxyketones

Autor(es)

Fernández Mateos, Alfonso

Encinas Madrazo, Soledad

Herrero Teijón, Pablo

Rubio González, María Rosa

Palabras clave

Química orgánica

Nitrilos

Radicales (Química)

Cloruros

Reacciones químicas

Clasificación UNESCO

2306 Química Orgánica

Fecha de publicación

2009

Citación

Fernández Mateos, A., Herrero Teijón, P., Encinas Madrazo, S. & Rubio González, R. (2009). Titanocene-Promoted Intermolecular Couplings of Epoxides with Nitriles. An Easy Access to β-Hydroxyketones. The Journal of Organic Chemistry, 74(10), 3913–3918. https://doi.org/10.1021/jo900479v

Resumen

[EN]Radical couplings of epoxides and nitriles mediated by Cp2TiCl provide a diastereoselective route to the synthesis of β-hydroxyketones. The conditions of this “aldol-like” reaction are mild enough to avoid the dehydration of the β-hydroxyketone. The scope of the coupling reaction with functionalized and tetrasubstituted epoxides has been studied. The radical character of the coupling reactions is demonstrated.

URI

https://hdl.handle.net/10366/154179

ISSN

0022-3263

DOI

10.1021/jo900479v

Versión del editor

https://doi.org/10.1021/jo900479v

Aparece en las colecciones