Novel heterogeneous ruthenium racemization catalyst for dynamic kinetic resolution of chiral aliphatic amines. Issue 1 (25th November 2019)

• Record Type: Journal Article
• Authors: Adriaensen, Koen; Vercammen, Jannick; Van Goethem, Cédric; Eyley, Samuel; Vankelecom, Ivo; Thielemans, Wim; De Vos, Dirk
• Is Part Of: Green chemistry. Volume 22:Issue 1(2020)
• Page Start: 85
• Page End: 93
• Publication Date: 2019-11-25
• Subjects: Environmental chemistry -- Industrial applications -- Periodicals; Environmental management -- Periodicals; 660
• DOI: 10.1039/c9gc02615k
• Languages: English
• ISSNs: 1463-9262

Abstract

Abstract : Only few dynamic kinetic resolution (DKR) systems are known for chiral aliphatic amines due to the difficult racemization of these 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%.