Exploring substrate scope of Shi-type epoxidations

Enantioselective epoxidations of alkenes (12 examples) were achieved using a Shi-type carbohydrate-derived hydrate and Oxone. The chiral platform provided by the catalyst tolerates a wide range of substituents providing high yields and enantioselectivities (80-95.5% ee). However, styrene derivatives were only converted with poor selectivities (11-26% ee).