Production of enantiopure β-amino-γ-hydroxyesters from benzoic acid by a selective formal aminohydroxylation

Abstract The enantioselective preparation of three protected β-amino-γ-hydroxyesters from benzoic acid is described. The employed synthetic methodology involves the ipso , ortho cis -dihydroxylation of benzoic acid by the mutant strain Ralstonia eutropha B9, followed by a selective halonium induced beta lactamization. Modification of this novel β-lactam structure by the appropriate sequence of reactions allows for the selective preparation of the aforementioned β-amino-γ-hydroxyesters in a diastereodivergent manner. The overall transformation results in a selective formal aminohydroxylation of the diene moiety of the initial cis -cyclohexadienediol. The synthesized products are important building blocks and will allow for the selective preparation of aminoacids, inosamines and alkaloids from benzoic acid.