Issue 1, 2020

Novel heterogeneous ruthenium racemization catalyst for dynamic kinetic resolution of chiral aliphatic amines

Abstract

Only few dynamic kinetic resolution (DKR) systems are known for chiral aliphatic amines due to the difficult racemization of these amines. In this work, each aspect of the DKR of aliphatic amines is investigated. Various ruthenium catalysts were evaluated to increase their applicability in racemization as an alternative to established heterogeneous palladium catalysts. A heterogeneous Ru(III) on zeolite catalyst showed good activity for racemization in aprotic polar media. Next, kinetic resolution was evaluated; excellent yields (50%) and selectivities (>99%) were obtained in apolar solvents when employing isopentyl propionate as resolving agent. After evaluation of both components, the complete dynamic kinetic resolution of an aliphatic amine was established with good selectivity (97%), enantiomeric excess (96%) and a yield exceeding the kinetic resolution limit of 50%.

Graphical abstract: Novel heterogeneous ruthenium racemization catalyst for dynamic kinetic resolution of chiral aliphatic amines

Supplementary files

Article information

Article type
Paper
Submitted
26 7 2019
Accepted
18 11 2019
First published
21 11 2019

Green Chem., 2020,22, 85-93

Novel heterogeneous ruthenium racemization catalyst for dynamic kinetic resolution of chiral aliphatic amines

K. Adriaensen, J. Vercammen, C. Van Goethem, S. Eyley, I. Vankelecom, W. Thielemans and D. De Vos, Green Chem., 2020, 22, 85 DOI: 10.1039/C9GC02615K

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