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.
Kinetic Resolution of Allylic Alcohols
We have developed an isothiourea-catalysed kinetic resolution of challenging allylic alcohols to form enantiomerically enriched alcohols and esters with high levels of selectivity. In this case, the catalyst must differentiate between an aryl and an alkenyl substituent on the carbinol. The scope of this process has been widely explored, with the use of a naphthyl substituent versus a vinyl substituent leading to an almost perfect kinetic resolution. The process can also be applied to allylic alcohols derived from monomers obtained from renewable lignin resources. Read more at: Chem. Eur. J. 2016, 22, 18916-18922.
We are interested in using 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.