Chemoenzymatic dynamic kinetic resolution of primary amines using a recyclable palladium nanoparticle catalyst together with lipases.
A catalyst consisting of palladium nanoparticles supported on amino-functionalized siliceous mesocellular foam (Pd-AmP-MCF) was used in chemoenzymatic dynamic kinetic resolution (DKR) to convert primary amines to amides in high yields and excellent ee's. The efficiency of the nanocatalyst at temperatures below 70 °C enables reaction conditions that are more suitable for enzymes. In the present study, this is exemplified by subjecting 1-phenylethylamine (1a) and analogous benzylic amines to DKR reactions using two commercially available lipases, Novozyme-435 (Candida antartica Lipase B) and Amano Lipase PS-C1 (lipase from Burkholderia cepacia) as biocatalysts. The latter enzyme has not previously been used in the DKR of amines because of its low stability at temperatures over 60 °C. The viability of the heterogeneous Pd-AmP-MCF was further demonstrated in a recycling study, which shows that the catalyst can be reused up to five times.
Department of Organic Chemistry, Arrhenius Laboratory, Stockholm University , SE-106 91 Stockholm, Sweden.
Karl P J
KP
Gustafson
Richard
R
Lihammar
Oscar
O
Verho
Karin
K
Engström
Jan-E
JE
Bäckvall
D000588:Amines / Q000737:chemistry* / Q000378:metabolism; D016956:Burkholderia cepacia / Q000201:enzymology; D002175:Candida / Q000201:enzymology; D002384:Catalysis; D004800:Enzymes, Immobilized; D005656:Fungal Proteins; D007700:Kinetics; D008049:Lipase / Q000737:chemistry* / Q000378:metabolism; D053768:Metal Nanoparticles / Q000737:chemistry*; D008958:Models, Molecular; D008968:Molecular Conformation; D010165:Palladium / Q000737:chemistry* / Q000378:metabolism; D013816:Thermodynamics
D000588:Amines; D004800:Enzymes, Immobilized; D005656:Fungal Proteins; D010165:Palladium; C093667:Novozyme 435; D008049:Lipase