A chemoenzymatic dynamic kinetic resolution protocol for the transformation of primary amines into amides in high yields and excellent ee's utilizing a racemization catalyst consisting of palladium nanoparticles immobilized on amino-functionalized siliceous mesocellular foam (Pd-AmP-MCF) was developed. The protocol enabled reaction temperatures below 70 �C, which are more suitable for enzymes. This was demonstrated by subjecting 1-phenylethylamine as well as analogous amines to a dynamic kinetic resolution using two commercially available lipases as resolving catalysts. The well-known CALB (Candida Antartica Lipase B) and the Lipase PS (lipase from Burkholderia Cepacia) were used, where the second enzyme is previously unreported in the DKR or amines, due to its low stability at temperatures over 60 �C. The recyclability of the heterogeneous Pd-AmP-MCF was further demonstrated by a recycling study where the nanocatalyst could be re-used up to five times. Acknowledgement:  Financial support from the Berzelius Center EXSELENT, the European Research Council (ERC AdG 247014), the Knut and Alice Wallenberg Foundation, and the Swedish Research Council are gratefully acknowledged.

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

248th National Meeting (2014)

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