Presenter: Mackay Steffensen
Authors: Cali Kucifer, Mackay Steffensen
Faculty Advisor: Mackay Steffensen
Institution: Southern Utah University
The Benzoin Condensation is a reaction that couples two aldehydes to form an α-hydroxyketone using an umpolung methodology, that reverses the polarity of the aldehyde to make it nucleophilic. This reaction was originally developed for the coupling of aromatic aldehydes. Advances in this reaction have increased the scope of possible coupling partners which now include options that do not contain aromatic groups. One option that has not been demonstrated is the coupling of an aromatic aldehyde with a cyclic ketone, to produce a benzylic ketone with an appended tertiary α-hydroxy cycloalkanol. Methods exist to create such a structural motif, but often require several steps, complex procedures, or expensive/toxic reagents. If successful, our efforts will expand the scope of benzoin-like condensations and ideally provide a rapid method to a useful class of molecules. Potential application of this reaction to the synthesis of a natural product will also be discussed.