Racemization of secondary‐amine‐containing natural products using heterogeneous metal catalysts

A1 Originalartikel i en vetenskaplig tidskrift (referentgranskad)

Interna författare/redaktörer

Publikationens författare: Barbara Kovács, Risto Savela, Karoliina Honkala, Dmitry Yu. Murzin, Enikő Forró, Ferenc Fülöp, Reko Leino
Publiceringsår: 2018
Tidskrift: ChemCatChem
Volym: 10
Nummer: 13
Artikelns första sida, sidnummer: 2893
Artikelns sista sida, sidnummer: 2899
eISSN: 1867-3899


Heterogeneously catalyzed racemization reactions of the secondary amines (S)‐1‐methyl‐6,7‐dimethoxy‐1,2,3,4‐tetrahydroisoquinoline (salsolidine) and (S)‐1‐methyl‐1,2,3,4‐tetrahydro‐ß‐carboline were investigated using Pd, Pt, and Ir on carbon or Al2O3 supports. A comparison of kinetics and deactivation on selected platinum and iridium catalysts was performed. Furthermore, the relative stabilities of (S)‐salsolidine and the corresponding imine on Pt(1 1 1) and Ir(1 1 1) surfaces were analyzed by density functional theory calculations. The racemization was faster on platinum and took place without detectable byproduct formation. Iridium, however, proved reusable and, in contrast to the platinum catalyst, deactivation at low catalyst concentration was not observed. Also, the physisorption of (S)‐salsolidine and the imine was stronger on platinum than on iridium.

Senast uppdaterad 2020-14-08 vid 04:58