Biomimetic epoxidation in aqueous media catalyzed by cyclic dipeptides

ABSTRACT

We have developed a practical epoxidation of electron-deficient enones in aqueous media using cyclic dipeptides as bioinspired green catalyst. Optimizing the reaction conditions in a triphasic system led to efficient conditions providing epoxides with good enantioselectivities. Depending on the catalyst substituent chirality, both enantiomers are obtained. The cyclic rigidity impacts significantly the enantioselectivity.

GRAPHICAL ABSTRACT

KEYWORDS:

• Asymmetric epoxidation
• bioinspired catalyst
• cyclic dipeptides
• diketopiperazines
• triphasic system

Acknowledgment

The authors thank François Otis for his professional assistance with liquid chromatography.