Research
The way in which synthetic organic chemistry is performed must undergo significant changes to meet the challenges of the 21st century. We are interested in developing new catalytic methodologies that convert simple, readily available starting materials into synthetically valuable compounds.
Boronic Acid Catalysis
We are interested in using simple, readily-available aryl boronic acids as catalysts for a variety of different processes. Aryl boronic acids are attractive potential catalysts as they are easily prepared, generally non-toxic and are easy to handle. Moreover, through varying the substituents on the aryl ring, the Lewis acidity of the boron centre may be modified. We are currently exploring the use of aryl boronic acids and boronic esters as catalysts in a range of different processes, including the activation of alcohols and conjugate addition reactions.
Catalytic Electrosynthesis
We are interested in the application of electrochemistry in organic synthesis. Electrochemical techniques for the manipulation of fine chemicals and pharmaceuticals are underdeveloped, but organic electrosynthesis has many benefits compared with traditional reagent-based transformations including high functional group tolerance, facile scalability, and inherent sustainability. While reactions can be performed directly at electrodes, we are interested in the use of small-molecule catalysts to facilitate electron-transfer to substrates in solution. Such mediators can lead to increased and/or new reaction selectivity and can amplify the potential gradient between the electrode and substrate, allowing the use of milder conditions.
Kinetic Resolution of Allylic Alcohols
We are interested in exploring the acylative kinetic resolution of challenging substrates using isothiourea-based organocatalysts in collaboration with Prof. Andrew Smith at the University of St Andrews. For example, we have developed an isothiourea-catalysed kinetic resolution of allylic alcohols to form enantiomerically enriched alcohols and esters with high levels of selectivity (Chem. Eur. J. 2016, 22, 18916). In this case, the catalyst must be able to differentiate between an aryl and an alkenyl substituent on the stereogenic carbinol centre. The scope of this process has been widely explored to investigate the parameters that effect the recognition event that is required to achieve high selectivity. The method has also been applied to the kinetic resolution of allylic alcohols derived from monomers obtained from renewable lignin resources, with the resulting products used as substrates in natural product synthesis (Org. Biomol. Chem. 2018, 16, 266).
