Abstract

We report herein a new and efficient four-step method for the stereoselective conversion of (-) diethyl (D)- and (+) diethyl (L)-tartrate into diethyl (2S,3S)-(+)-2,3-epoxysuccinate and diethyl (2R,3R)-(-)-2,3- epoxysuccinate respectively. We also applied this synthetic method to prepare a C-2 symmetric epoxide, a key chiral intermediate, employed in the total synthesis of natural products.

Keywords: Cyclic orthoformate, bromohydrin, enantiomers, epoxide