The enantio- and diastereoselective cross-annulation of cinnamaldehyde (6) and 2,2,2-trifluoroacetophenone (7) was examined to evaluate the performance of newly developed chiral bicyclic imidazolium salts 3 and 4 as catalyst precursors. The reaction proceeded to give desired gamma-lactone 8 with high diastereoselectivities (up to 10/1) and moderate enantioselectivities (up to 71% ee) when the sterically demanding catalyst precursors were used.