| Description |
The Wacker oxidation is a well-known and widely utilized reaction in synthetic organic chemistry for the transformation of terminal alkenes to methyl ketones using catalytic palladium. The recently described tert-butyl hydroperoxide (THBP)-mediated Wacker oxidation using the quinoline-oxazoline (Quinox) ligand has proven to be a ligand-controlled transformation with broad tolerance for a wide range of classical, challenging substrates with varying functionality. The development of an asymmetric variant of this reaction is necessary to broaden its utility. A kinetic resolution applied to Wacker transformations of acyclic substrates has not yet been described in the literature, and the utility of the resultant enantioenriched starting materials and products make it a compelling goal. Described herein is the development of a kinetic resolution for the TBHPmediated Wacker oxidation of terminal alkene substrates. A detailed mechanistic study of the symmetric transformation, as well as prior work performed by previous group members, provided the foundation for the approach to ligand modulation, succeeded by solvent, substrate, and counter ion optimization. Though optimal results have not yet been achieved, significant insight into each of these reaction parameters has been garnered for further study and progression of this methodology. |
