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 te...

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Bibliographic Details
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
Description
Summary: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;

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