Starting from the chiral 5,6,7,8-tetrahydroquinolin-8-ol core, a series of amino-phosphorusbased ligands was realized. The so-obtained amino-phosphine ligand (L1), amino-phosphinite (L2) and amino-phosphite (L3) were evaluated in iridium complexes together with the heterobiaryl diphosphines tetraMe-BITIOP (L4), Diophep (L5) and L6 and L7 ligands, characterized by mixed chirality. Their catalytic performance in the asymmetric hydrogenation (AH) of the model substrate 6,7-dimethoxy-1-phenyl-3,4-dihydroisoquinoline 1a led us to identify Ir-L4 and Ir-L5 catalysts as the most eective. The application of these catalytic systems to a library of dierently substituted 1-aryl-3,4-dihydroisoquinolines aorded the corresponding products with variable enantioselective levels. The 4-nitrophenyl derivative 3b was obtained in a complete conversion and with an excellent 94% e.e. using Ir-L4, and a good 76% e.e. was achieved in the reduction of 2-nitrophenyl derivative 6a using Ir-L5.
Asymmetric Hydrogenation of 1-aryl substituted-3,4-Dihydroisoquinolines with Iridium Catalysts Bearing Different Phosphorus-Based Ligands / G. Facchetti, M.S. Christodoulou, E. Binda, M. Fus(`(e)), I. Rimoldi. - In: CATALYSTS. - ISSN 2073-4344. - 10:8(2020 Aug 10).
|Titolo:||Asymmetric Hydrogenation of 1-aryl substituted-3,4-Dihydroisoquinolines with Iridium Catalysts Bearing Different Phosphorus-Based Ligands|
FACCHETTI, GIORGIO (Primo) (Corresponding)
CHRISTODOULOU, MICHAIL (Secondo)
RIMOLDI, ISABELLA (Ultimo) (Corresponding)
|Parole Chiave:||atropoisomeric chirality; chiral diphosphines; amino phosphine; imines reduction; iridium complexes;|
|Settore Scientifico Disciplinare:||Settore CHIM/03 - Chimica Generale e Inorganica|
Settore CHIM/06 - Chimica Organica
|Data di pubblicazione:||10-ago-2020|
|Digital Object Identifier (DOI):||http://dx.doi.org/10.3390/catal10080914|
|Appare nelle tipologie:||01 - Articolo su periodico|