Combination of a UPO-Based Epoxidation With a Subsequent Ring-Opening Reaction for the Synthesis of Amino Alcohols

This study presents the design to aim for an atom-efficient chemo-enzymatic synthesis route towards aromatic amino alcohols, based on an unspecific peroxygenase-catalysed oxyfunktionalisation of styrene and a highly atom-efficient conversion of the resulting epoxide with nucleophiles and electrophiles, respectively. This synthesis strategy features a simple two-step approach, and the practicality has been demonstrated at a semi-preparative scale. In a first step, the unspecific peroxygenase oxyfunctionalises the substrate, forming an epoxide. Due to its properties, the latter can serve as a starting material for the conversion into a wide range of products, thereby enabling the production of amino alcohols that are otherwise often difficult to synthesise. The shown concept features a one-pot two-step approach, depending on the respective ring-opening reagent. This method aims for a direct synthesis route for the pharmaceutical industry with good yields and high atom efficiency.