The introduction of a chiral centre into a non-chiral starting material is hard to achieve using traditional methods of chemical synthesis. Nevertheless, it is very important to obtain efficient methods by which to do so, as pure enantiomers of chiral compounds are of great importance to e.g. the pharmaceutical industry. One way in which chirality may be created is through the application of enzymes that are capable of enantioselectively functionalising a target molecule. For example, the flavin-dependent oxidoreductase vanillyl alcohol oxidase (VAO) can catalyse the enantioselective hydroxylation of 4-alkylphenols at the Cα position, leading to the formation of the (R)-enantiomer of the corresponding alcohol in high enantiomeric excess. To demonstrate that this enzyme can be used to produce chiral secondary alcohols on a synthetically relevant scale, we employed it in the enantioselective hydroxylation of the non-chiral aromatic compound 4-ethylphenol to yield (R)-1-(4′-hydroxyphenyl)ethanol. The protocol described here provides a detailed practical description of how this synthesis can be performed at a scale of 10 g of starting material.
|Title of host publication||Applied Biocatalysis|
|Subtitle of host publication||The Chemist's Enzyme Toolbox|
|Editors||John Whittall, Peter W. Sutton|
|Publication status||Published - Aug 2020|