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Enantiopure ethyl 2,3-dibromopropionate: Enantioselective synthesis vs preparative HPLC enantioseparation of racemate on multigram scale.
Chirality ( IF 2 ) Pub Date : 2020-06-22 , DOI: 10.1002/chir.23260
Hong-Ngoc Pham 1, 2 , Axelle Arrault 1 , Nicolas Vanthuyne 3 , Samir Acherar 1
Affiliation  

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.

中文翻译:

对映体纯的2,3-二溴丙酸乙酯:对映体选择性合成与制备型HPLC的外消旋体对映体的分离(以克为单位)。

外消旋的2,3-二溴丙酸乙酯,是低价出售的关键中间体,用于合成许多生物活性化合物中存在的几种杂环片段。令人惊讶地,对映异构体不是可商购的,并且从未在文献中描述。在这项工作中,我们采用了两种不同的策略来获得这些对映异构体,即对映异构体的合成和市售消旋物的合成HPLC对映体的分离(以克为单位)。第一种策略已被证明是不适当的,因为在合成过程中发生了消旋作用(ee≈9-50%)。相反地​​,第二种策略以克数为单位,可以很好地分离出市售消旋体(对映体的ee> 99.5%)。
更新日期:2020-06-22
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