Chiral (salen)Mn(m)Cl complexes catalyze epoxidation of cyclic 1,3-dienes with moderate-to-good enantioselectivity. A new catalyst (2), bearing sterically hindered and electron donating OSi(iPr)(3) (OTIPS)substituents, induces up to 12% higher selectivity than the previously-reported tert-butyl substituted analog 1.