Chemoenzymatic Dynamic Kinetic Resolution of Primary Amines Using a Recyclable Palladium Nanoparticle Catalyst Together with Lipases

• Published in: The Journal of Organic Chemistry
• Main Authors: Gustafson, Karl P. J., Lihammar, Richard, Verho, Oscar, Engström, Karin, Bäckvall, Jan-Erling
• Format: Article in Journal/Newspaper
• Language: English
• Published: Stockholms universitet, Institutionen för organisk kemi 2014
• Subjects: Organic Chemistry; Organisk kemi; antartic*
• Online Access: http://urn.kb.se/resolve?urn=urn:nbn:se:su:diva-104395; https://doi.org/10.1021/jo500508p

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 degrees 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 degrees 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. AuthorCount:5;