Diastereoselective synthesis of 7,8-carvone epoxides

Abstract

The synthesis of the two 7,8-epoxides of carvone has been attained using organocatalysis in a two-step synthetic route through a bromoester intermediate. Among the different reaction conditions tested for the bromination reaction, moderate yields and diastereoselection are achieved using proline, quinidine, and diphenylprolinol, yielding the corresponding bromoesters that were transformed separately into their epoxides, obtaining the enantiopure products.