One-pot hydroaminomethylation of an alkene under formation of primary amines by combining hydroformylation at elevated syngas pressure and biocatalytic transamination in water

Abstract

We report a novel one-pot chemoenzymatic synthesis of primary amines, combining rhodium-catalysed hydroformylation of styrene with transaminase-catalysed enzymatic transamination. This process is starting from styrene at 50 mM substrate loading on a 10 mL preparative scale. Combined towards a one-pot process with both steps running concurrently, this chemoenzymatic synthesis involves a 6-DPPon/rhodium-catalysed hydroformylation of styrene at 20 bar of syngas, forming the iso- and n-aldehydes and an enzymatic transamination of the in situ-formed aldehydes to the corresponding primary amines catalysed by the aminotransferase from Chromobacterium violaceum, yielding the desired primary amines with 99% conversion.