Hydrolytic Kinetic Resolution of Epoxides Catalyzed by Chromium(III)‐endo,endo‐2,5‐diaminonorbornane‐salen [Cr(III)‐DIANANE‐salen] Complexes. Improved Activity,Low Catalyst Loading

The hydrolytic kinetic resolution (HKR) of terminal epoxides, using chiral chromium(III )‐salen catalysts based on DIANANE (endo,endo‐2,5‐diaminonorbornane), was studied. A broad substrate scope was found for the chromium(III )‐DIANANE catalysts, and very low loadings (down to 0.05 mol %) were needed to achieve high enantiomeric purities of both the remaining epoxides and the product diols (up to >99 % ee). Besides monosubstituted epoxides, 2‐methyl‐2‐n‐pentyloxirane, which is an example for 2,2‐disubstituted epoxides, could be ring‐opened in an asymmetric fashion with water in the presence of an electronically tuned chromium(III )‐DIANANE complex.