Our investigation began with a screen of cinnamyl alcohol leaving groups and revealed that a strongly basic leaving group is necessary for a productive reaction (Figure ). Cinnamyl acetates resulted in no conversion to the desired product, and only SIA starting material was recovered. We hypothesized that the acetate anions, generated from reaction of palladium with the cinnamyl acetates, are not sufficiently basic to deprotonate the SIA and generate the SIA anion. The addition of one equivalent of potassium t-butoxide to the reaction with cinnamyl acetate provided the desired allylated SIA. The t-butyl carbonate leaving group was found to promote the desired reaction as, after palladium ionization, t-BuO -is liberated and obviates the need to charge exogenous base. With basic reactivity in hand, we turned to high throughput screening (HTS) to quickly identify reaction conditions to provide the desymmetrization products in high yield and enantioselectivity. The 96 well plate was divided into two halves for electrophiles t-butyl cinnamyl carbonate E1 and tbutyl (2-phenylallyl) carbonate E2 because of their success in other asymmetric alkylation reactions. Six different commercially available Trost-type ligands were screened against eight different solvents belonging to the following classes: ethereal, halogenated, aromatic, polar aprotic, and polar protic. A heat map measuring both the conversion and enantioselectivity for each reaction was constructed based on UV traces from the chiral UPLC data (Figure ). The yellow outer ring of the graph indicates percent conversion of starting material to allylated product. The inner green ring of the graph is the enantiomeric excess (ee) of the product formed. The absolute value of ee was used to normalize for the different enantiomers of catalyst used.