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

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

Journal Name: Letters in Organic Chemistry

Volume 3 , Issue 1 , 2006

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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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Article Details

VOLUME: 3
ISSUE: 1
Year: 2006
Page: [45 - 47]
Pages: 3
DOI: 10.2174/157017806774964512

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