A synthetic route for the preparation of enantio enriched chromenes is presented. From reducing the effects of tachycardia (elevated heart rate), to a novel smallpox vaccination, these benzopyran derivatives compromise motifs found in a plethora of pharmaceutical products. The novelty of our synthetic approach derives from the use of the enzyme oxynitrilase to induce the proper asymmetry in the achiral starting material. Two key steps, the palladium mediated 1,3 chiral transposition and the Grubbs catalyzed ring closing metathesis yield the corresponding monosubstituted chromene. A total of four chromenes (three enzyme direct, and one enzyme indirect) were successfully characterized by NMR and GCMS analysis.