Merging Regiodivergent Catalysis with Atom‐Economical Radical Arylation

A titanocene‐catalyzed regiodivergent radical arylation is described that allows access to either enantiomerically pure tetrahydroquinolines or indolines from a common starting material. The regioselectivity of epoxide opening that results in the high selectivity of heterocycle formation is controll...

Descripción completa

Detalles Bibliográficos
Autores principales: Mühlhaus, Felix, Weißbarth, Hendrik, Dahmen, Tobias, Schnakenburg, Gregor, Gansäuer, Andreas
Formato: Online Artículo Texto
Lenguaje:English
Publicado: John Wiley and Sons Inc. 2019
Materias:
Communications
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6852184/
https://www.ncbi.nlm.nih.gov/pubmed/31394024
http://dx.doi.org/10.1002/anie.201908860
Descripción
Sumario:A titanocene‐catalyzed regiodivergent radical arylation is described that allows access to either enantiomerically pure tetrahydroquinolines or indolines from a common starting material. The regioselectivity of epoxide opening that results in the high selectivity of heterocycle formation is controlled by two factors, the absolute configuration of the enantiopure ligands of the (C(5)H(4)R)(2)TiX(2) catalyst and the inorganic ligand X (X=Cl, OTs). The overall reaction is atom‐economical and constitutes a radical Friedel–Crafts alkylation.

Ejemplares similares