Ligand and base additive effects on the reversibility of nucleophilic addition in palladium-catalyzed allylic aminations monitored by nucleophile crossover
Nucleophile crossover quantitates reversibility of benzylamine addition. DBU and Cs2CO3 inhibit crossover/reversibility with all ligands tested. Cs2CO3 causes much less elimination to dienes than DBU. Percent conversion analysis shows timing of crossover/reversibility. Results support reversibility as mechanism for base effects on enantioselectivity.