The first organocatalyzed asymmetric method for the synthesis of dihydrodibenzofurans based on a dienamine process has been developed. This two-step protocol works with a broad range of substrates and delivers only the cis-diastereomer in good yield with up to 91% ee. The enantioenriched products have been transformed to highly functionalized and partially hydrogenated dibenzofurans in excellent diastereoselectivities.