On Ligand Design for Catalytic Outer Sphere Reactions: A Simple Asymmetric Synthesis of Vinylglycinol

摘要

The importance of enantiomerically pure vinylglyciriol as a building block has stimulated much synthetic effort. Not only is it an obvious precursor of vinylglycine; nianv biologically important targets may be derived from it. such as the tuberculostatic (+)-ethambutol, the antimetabolite antibiotic acivicin, the antibiotic phosphinotriein, the selective enzyme-activated inhibitor of GABA-T vigubatrin, an inhibitor of calmodulin-activatcd brain phosphodicstcrase pscudodistomin B, adcnosme deamimase inhibitor pentostatin, metal-chelating polyamino acid aspergillomarasamine A, and the antibiotic subunit galatinic acid. The most effective syntheses of vinylglydne to date begin with ammo acids, only one enantiomer of which is generally available inexpensively. Therefore, a simple asymmetric synthesis that would provide access to both enantiomers is most desirable.