Dynamic Resolution of Boronic Esters: A Powerful Strategy for Asymmetric Atropisomer Synthesis

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Atropisomers are an unusual class of molecules in organic chemistry as they convey a defined three-dimensional shape from flat molecular fragments. Atropisomerism arises from hindrance of bond rotation about single bonds due to steric clashes, thereby making the isolation of the individual isomers possible. There are a large number of prominent molecules derived from nature as well as pharmaceuticals that exhibit atropisomerism, however stereoselective synthetic methods towards these compounds remain very challenging. We have developed a way to access specific atropisomers with high selectivity that involves the equilibration of an easily prepared stereoisomeric mixture. This method is underpinned by the chemistry of boron, which serves to both control atropisomer stereochemistry, while acting as a handle for further chemical modifications. We are only just beginning to understand the scope of this process, but we believe that it will represent a general method for preparing these important compounds. The requested grant will allow us to demonstrate the potential of the methodology, and will show that we can use it to access a very broad range of high value chemicals.