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Dehydroabietic acid-based chiral ionic liquids: Their synthesis and potential enantiomeric recognition ability
Tetrahedron ( IF 2.1 ) Pub Date : 2020-09-06 , DOI: 10.1016/j.tet.2020.131567
Yi Zhu , Li Ge , Yuxin Chen , Yande Chen , Yu Liang , Yidan Wang , Kedi Yang

Several new chiral imidazolinium ionic liquids (CILs) have been synthesized by using optically pure dehydroabietic acid (DA) as the chiral precursor. Their enantiomeric recognition abilities were measured using rac-mandelic acid n-Bu4N salt as the substrate by NMR spectroscopy. Based on the structure-interaction relationships, the bulky anion and the side chain linking the DA group to the imidazole ring have crucial effects on CIL recognition. The 1H NMR measurements indicated that [MimMeDA]NTf2 exhibits good and versatile molecular recognition ability. The new DA-based CILs reported here may be interesting chiral media for enantioselective reactions and useful in enantiomeric separations.



中文翻译:

基于脱氢松香酸的手性离子液体:它们的合成和潜在的对映体识别能力

通过使用光学纯的脱氢松香酸(DA)作为手性前体,合成了几种新型手性咪唑啉鎓离子液体(CIL)。通过rac-扁桃酸n- Bu 4 N盐作为底物通过NMR光谱法测量它们的对映体识别能力。基于结构-相互作用关系,大阴离子和连接DA基团与咪唑环的侧链对CIL识别具有关键作用。的1个1 H NMR测量表明,[MimMeDA] NTF 2显示出良好的和通用的分子识别能力。此处报道的新的基于DA的新CIL可能是用于对映选择性反应的有趣手性介质,可用于对映体分离。

更新日期:2020-10-12
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