Stereospecific preparation of glycidic esters from 2-chloro-3-hydroxyesters. Application to the synthesis of (2R, 3S)-3-phenylisoserine

O Cabon, D Buisson, M Larcheveque, R Azerad

Index: Cabon; Buisson; Larcheveque; Azerad Tetrahedron Asymmetry, 1995 , vol. 6, # 9 p. 2211 - 2218

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Citation Number: 31

Abstract

Cis-and trans-glycidic esters may be synthesized in high enantiomeric purities by cyclisation with potassium carbonate in DMF of the corresponding syn-or anti-2-chloro-3-hydroxyesters, prepared by microbial reduction of 2-chloro-3-oxoesters. In contrast, more basic media such as sodium ethylate afford exclusively the trans-isomer, whatever the stereochemistry of the starting 2-chloro-3-hydroxyester is. Cyclisation of deuterated compounds showed that this ...