Rhodium(I)-Complexes Catalyzed 1,4-Conjugate Addition of Arylzinc Chlorides to N-Boc-4-pyridone

Rhodium(I)-complexes catalyzed the 1,4-conjugate addition of arylzinc chlorides to N-Boc-4-pyridone in the presence of chlorotrimethylsilane (TMSCl). A combination of [RhCl(C(2)H(4))(2)](2) and BINAP was determined to be the most effective catalyst to promote the 1,4-conjugate addition reactions of...

Descripción completa

Detalles Bibliográficos
Autores principales: Guo, Fenghai, McGilvary, Matthew A., Jeffries, Malcolm C., Graves, Briana N., Graham, Shekinah A., Wu, Yuelin
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2017
Materias:
Article
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6154701/
https://www.ncbi.nlm.nih.gov/pubmed/28468302
http://dx.doi.org/10.3390/molecules22050723
Descripción
Sumario:Rhodium(I)-complexes catalyzed the 1,4-conjugate addition of arylzinc chlorides to N-Boc-4-pyridone in the presence of chlorotrimethylsilane (TMSCl). A combination of [RhCl(C(2)H(4))(2)](2) and BINAP was determined to be the most effective catalyst to promote the 1,4-conjugate addition reactions of arylzinc chlorides to N-Boc-4-pyridone. A broad scope of arylzinc reagents with both electron-withdrawing and electron-donating substituents on the aromatic ring successfully underwent 1,4-conjugate addition to N-Boc-4-pyridone to afford versatile 1,4-adducts 2-substituted-2,3-dihydropyridones in good to excellent yields (up to 91%) and excellent ee (up to 96%) when (S)-BINAP was used as chiral ligand.

Ejemplares similares