A new C2 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鈭扐lder reaction and the Nozaki鈭扝iyama鈭扠ishi reaction with high efficiency and excellent stereoselectivity.