Chemoenzymatic dynamic kinetic resolution of primary amines using a recyclable palladium nanoparticle catalyst together with lipases

J Org Chem. 2014 May 2;79(9):3747-51. doi: 10.1021/jo500508p. Epub 2014 Apr 23.

Abstract

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.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amines / chemistry*
  • Amines / metabolism
  • Burkholderia cepacia / enzymology
  • Candida / enzymology
  • Catalysis
  • Enzymes, Immobilized
  • Fungal Proteins
  • Kinetics
  • Lipase / chemistry*
  • Lipase / metabolism
  • Metal Nanoparticles / chemistry*
  • Models, Molecular
  • Molecular Conformation
  • Palladium / chemistry*
  • Palladium / metabolism
  • Thermodynamics*

Substances

  • Amines
  • Enzymes, Immobilized
  • Fungal Proteins
  • Palladium
  • Novozyme 435
  • Lipase