Building on structural and mechanistic studies of lithiated enolates derived from acylated oxazolidinones (Evans enolates) and chiral lithiated amino alkoxides, we have found that amino alkoxides amplify the enantioselectivity of aldol additions. Pairing enantiomeric series afford matched and mismatched stereoselectivities. The structures of mixed tetramers showing 2:2 and 3:1 (alkoxide-rich) stoichiometries are determined spectroscopically. Rate and computational studies provide a viable mechanistic and stereochemical model based on direct reaction of the 3:1 mixed tetramers and unanswered questions for the 2:2 mixed aggregates.