Design and synthesis of chiral ketones for catalytic asymmetric epoxidation of unfunctionalized olefins

The synthesis of a series of novel C2 symmetrical chiral ketones and their activities in catalytic asymmetric epoxidations are described. The first cyclic ketone obtained from the process acted as the ideal template for the introduction of chiral elements. Results also showed that the ester groups that provide rigid and C2 symmetric structures to the cyclic ketones significantly influence the effectiveness of asymmetric epoxidations.