With the successful synthesis of (-)-tedanalactam, we have accomplished the original goal of our studies -the application of our asymmetric catalytic method for the preparation of cis-a,b-epoxyamides (from aldehydes and diazoacetamides using a chiral borate catalyst containing a VANOL ligand) to the synthesis of 3,4-epoxy-2-piperidone alkaloids. Critical failures in our exploratory studies towards achieving this goal led to the design and discovery of a new catalyst system involving a chiral aluminate catalyst containing a VANOL ligand that is structurally analogous to the borate catalyst. Synthetic studies have established the scope and computational investigations have elucidated the origin of the enantiodivergence observed upon switching from boron to aluminum. We are currently evaluating the generality of enantiodivergence in other catalytic asymmetric reactions of aldehydes.