A Convenient Preparation of Enantiomerically Pure Esters of trans- Epoxysuccinic Acid

Demetris   P.   Papahatjis; Therapia      Kourouli; Victoria   R.   Nahmias

doi:10.2174/157017806774964512

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

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Letters in Organic Chemistry

Title: A Convenient Preparation of Enantiomerically Pure Esters of trans- Epoxysuccinic Acid

Volume: 3 Issue: 1

Author(s): Demetris P. Papahatjis, Therapia Kourouli and Victoria R. Nahmias

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Keywords: Cyclic orthoformate, bromohydrin, enantiomers, epoxide

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.

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Papahatjis P. Demetris, Kourouli Therapia and Nahmias R. Victoria, A Convenient Preparation of Enantiomerically Pure Esters of trans- Epoxysuccinic Acid, Letters in Organic Chemistry 2006; 3 (1) . https://dx.doi.org/10.2174/157017806774964512