Dehydroabietic acid-based chiral ionic liquids: Their synthesis and potential enantiomeric recognition ability. Issue 44 (30th October 2020)

• Record Type: Journal Article
• Authors: Zhu, Yi; Ge, Li; Chen, Yuxin; Chen, Yande; Liang, Yu; Wang, Yidan; Yang, Kedi
• Is Part Of: Tetrahedron. Volume 76:Issue 44(2020)
• Publication Date: 2020-10-30
• Subjects: Dehydroabietic acid -- Chiral ionic liquids -- Chiral recognition -- Mandelic acid; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tet.2020.131567
• Languages: English
• ISSNs: 0040-4020

Abstract

Abstract: 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 -Bu4 N 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 1 H 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. Graphical abstract: Image 1 Highlights: Several new dehydroabietic acid-based chiral imidazolinium Ionic Liquids (DA-CILs) have been synthesized. The Δδ of 1 H-NMR was used to investigate the chiral discrimination of DA-CILs. The DA-CILs with NTf2 exhibit good chiral recognition ability for n -Bu4 N salts of racemic mandelic acid and its derivatives.