The isopropyl (2R,3R)- and (2S,3S)-cis-2,3-epoxybutanoates were prepared in three steps from L- and D-threonine, respectively. The racemic isopropyl trans-2,3-epoxybutanoate was obtained in two steps from trans-crotonic acid. The previous esters (four stereoisomers) could be easily differentiated by gas chromatography on a CP-Chirasil-Dex-CB capillary column. (C) 1999 Elsevier Science B.V. All rights reserved.
Demillequand, M., Cérésiat, M., Belmans, M., Kemps, L., & Marchand-Brynaert, J. (1999). Analytical separation of the four stereoisomers of isopropyl 2,3-epoxybutanoate by gas chromatography. Journal of Chromatography A, 832(1-2), 259-264. https://doi.org/10.1016/S0021-9673(98)00951-0 (Original work published 1999)