Enantiopure ethyl 2,3-dibromopropionate: Enantioselective synthesis vs preparative HPLC enantioseparation of racemate on multigram scale.
Fiche publication
Date publication
juin 2020
Journal
Chirality
Auteurs
Membres identifiés du Cancéropôle Est :
Dr ARRAULT Axelle
Tous les auteurs :
Pham HN, Arrault A, Vanthuyne N, Acherar S
Lien Pubmed
Résumé
Racemic ethyl 2,3-dibromopropionate, commercially available at low price, is a key intermediate used in the synthesis of several heterocycle fragments, which are present in many biologically active compounds. Surprisingly, the enantiomers are not commercially available and have never been described in the literature. In this work, we undertook two different strategies to obtain these enantiomers, which are enantioselective synthesis and preparative HPLC enantioseparation of commercially available racemate on multigram scale. The first strategy has proved inadequate because racemization occurred during the synthesis (ee ≈ 9-50%). Conversely, the second strategy produced a very good enantioseparation of commercially available racemate (ee > 99.5% for both enantiomers) on multigram scale.
Mots clés
chiral stationary phases, enantioselective chromatography, ethyl 2,3-dibromopropionate, preparative resolution, racemization
Référence
Chirality. 2020 Jun 22;: