Chiral epoxides are important intermedi- ates in chemistry and: biology. The high-throughput screening of asymmetric epoxidation conditions requires fast determination of the absolute configurations and ee values of chiral epoxides. Herein, we report molecular recognition and chiroptical sensing of epoxides in water using endo-functionalized molecular tubes. The absolute configurations and ee values were simultaneously determined by circular dichroism spectroscopy. In addition, real-time monitoring as well as the application to real asymmetric epoxidation was demonstrated. The method is simple, environmentally friendly, and amenable to high throughput screening.