Initial chiral ligands screening. The review of the previously discussed literature on the asymmetric synthesis of BDQ (3) suggests that chiral ethanolamines (containing an N-C-C-O bond structure) can promote significant stereoinduction via transfer of chirality in the 1,2-addition step (Scheme 2). While the exact transition state for this chirality transfer is unknown, the impact of additives like LiBr seems to suggest that higher-order aggregation is critical for the associated chiral amine to promote stereoselectivity in this reaction. Indeed, lithium salt additives influence diastereoselectivity during lithiation reactions and are capable of affecting the geometry, equilibrium, and rate of assembly or dissociation of lithium aggregates. These early examples encouraged us to further investigate the use of chiral lithium amide bases possessing the chiral ethanolamine substructure to invoke chiral induction in the BA reaction. Herein, the use of lithium chiral amides to induce both diastereo-and enantioselectivity during the lithiation/1,2-addition steps in the BDQ (3) synthesis is reported for the first time.