A new C 2 symmetric salen scaffold based on cis-2, 5-diaminobicyclo [2.2. 2] octane has been synthesized that forms complexes with a wide range of metals. The chromium (III) complex is shown to catalyze the hetero-Diels− Alder reaction and the Nozaki− Hiyama− Kishi reaction with high efficiency and excellent stereoselectivity.