In seeking an effective chiral transfer agent for this transformation, approximately 25 chiral amines containing the aforementioned ethanolamine substructure were screened; the majority of them derived from D/L-amino acids (alanine, leucine, isoleucine, threonine, valine, and proline) (see Supporting Information, Scheme S10 for complete list). At first, the chiral amines were used in combination with lithium pyrrolidide as the base for the lithiation step (Scheme 3). All of the screened chiral amines afforded some level of influence on stereoselectivity towards BDQ (3) or ent-3, ranging from 1.5:1 to 10:1 d.r. (syn:anti) and overall assay yields from 30 to 78 %. Moreover, the enantioselectivity towards BDQ (3) varied from 2 to 26 % ee.