The ability to perform a dynamic kinetic asymmetric transformation (DYKAT) using the palladiumcatalyzed asymmetric allylic alkylation (AAA) is explored in the context of butadiene monoepoxide. The versatility of this commercially available, but racemic, four-carbon building block becomes significantly enhanced via conversion of both enantiomers into a single enantiomeric product. The concept is explored in the context of a synthesis of vinylglycinol with phthalimide as the nitrogen source. The success of the project required a new design of the ligand for palladium wherein additional conformational restraints were introduced. Thus, the phthalimide derivative of vinylglycinol was obtained in nearly quantitative yield and had an ee of 98% which, upon crystallization, was enhanced to >99%. This one-step synthesis of a protected form of vinylglycinol provided short practical syntheses of the title compounds. Vigabatrin requires only four steps, and ethambutol six. The intermediate to the existing synthesis of ethambutol is available in 87% yield in three steps. (R)-Serine derives from oxidative cleavage of the double bond. The reaction of phthalimide and isoprene monoepoxide demonstrates the remarkable ability of the chiral ligands to control both regioselectivity and enantioselectivity and demonstrates the effectiveness of this protocol in creating a quaternary center asymmetrically.While, in theory, there are many mechanisms for asymmetric induction with transition metal catalysts, in practice, the overwhelming mechanism comes down to the differentiation of enantiotopic faces of prochiral unsaturation (alkenes, carbonyl groups, etc.). 1 The metal-catalyzed allylic alkylation may employ a similar mechanism; however, in most cases, it involves some other enantiodiscriminating events such as discriminating between enantiotopic leaving groups or enantiotopic termini of π-allylmetal interemediates. 2 An unsymmetrical substrate such as 1 (Scheme 1) may lead preferentially to either complex 2 or 3 to give rise to an asymmetric alkylation. On the other hand, it may give a mixture of 2 and 3 which can equilibrate via a σ-complex. In this case, the enantiodiscrimination arises because of a rate differential between the reaction of the two diastereomeric complexes 2 and 3 and the nucleophile to give either enantiomeric product 4 or ent-4. In this latter scenario, employing the racemate 7 and ent-7 also may lead to asymmetric induction. This type of process, while frequently referred to as a kinetic resolution, is more properly referred to as a dynamic kinetic asymmetric transformation (DYKAT). Using the family of ligands being developed in these laboratories, 3 our mnemonic predicts the complex derived from ligand 5 and Pd(0) should favor path a; whereas, the complex derived from ligand 6 and Pd(0) should favor path b. The major problem with this series is the issue of regioselectivity since attack in such systems is normally favored at the primary carbon which generates an achiral product. 4