Use of chiral lithium amides to promote quinoline 1 deprotonation. During the aforementioned screening (Scheme 3), it was found that amines 11, 12, 13, 14, and 15 resulted in the highest enantioselectivity, providing BDQ (3) in 20 to 26 % ee (see Supporting Information). These chiral amines were reevaluated in the absence of lithium pyrrolidide; the objective being to analyze if the lithium chiral amides obtained from those molecules would be basic enough to promote quinoline 1 deprotonation by themselves (Scheme 4). The acyclic lithium amides derived from 12, 13, 14, and 15 did not show any reaction in the absence of an external base. Notably, the lithium amide base of (R)-2-(methoxymethyl)pyrrolidine ( ) promoted quinoline 1 lithiation and afforded a 53 % assay yield of the syn + anti-diastereomers, in addition to the d.r. and enantiomeric excess (ee) favoring BDQ (3) (~8:1 and 26 % ee, respectively) (Scheme 4). Despite the fact that base 11 yielded only 30 % of BDQ (3), the same yield as in the M4ALL's non-chiral approach, it is important to highlight that this constitutes the first example of the usage of chiral lithium amide bases directly to promote both diastereo-and enantioselectivity in the current BA reaction. For this reason, amine 11 was selected for further optimization studies. Our main goal was to analyze if modifications in the reaction conditions would allow higher starting materials conversion, and consequently increase the yield of BDQ (3).