Our investigation of β-alkoxy N-Ts imines utilizes 1,3 asymmetric induction to access anti-1,3 amino alcohols. Furthermore, the observed diastereomeric ratios provide insight into: (1) the influence of the conformational preferences of the six-membered ring chelate (2) the origin of selectivity when BF3•OEt2, a non-chelateable Lewis acid, is employed. The results of our investigation can help to construct a generalized model that describes the diastereomeric outcomes of additions to β-alkoxy carbon electrophiles.