A highly regio-, chemo-, and stereoselective cascade process initiated by enantioselective iminium-catalyzed conjugate addition of 2-hydroxycinnamaldehydes and 2-oxocarboxylic esters is presented. Normal cinnamaldehydes are not reactive under the same reaction conditions. Bridged bicyclic ketals rather than acetals bearing stereocenters on both the bridge carbon and bridgehead ketal carbon are synthesized.