Chiral Ionic Liquids, a Renewal for the Chemistry of Chiral Solvents? Design, Synthesis and Applications for Chiral Recognition and Asymmetric Synthesis

Baudequin, Christine; Brégeon, Delphine; Levillain, Jocelyne; Guillen, Frédéric; Plaquevent, Jean‐Christophe; Gaumont, Annie‐Claude

doi:10.1002/chin.200615238

Cited by 12 publications

(20 citation statements)

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“…The presence of N,C-dialkyl indoles (6) in the reaction products might be caused by subsequent alkylation of either the N-alkyl compound (4) or the C-alkyl compound (5). To investigate the possibility of further alkylation, N-butyl indole (4) was treated with 1-iodobutane in [bmim] [Br] at 65…”

Section: Resultsmentioning

confidence: 99%

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Alkylation of ambident indole anion in ionic liquids

et al. 2007

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Section: Resultsmentioning

confidence: 99%

“…The exploitation of ionic liquids (IL) in transformations of organic substances has boomed during the last ten years [1][2][3][4][5][6][7][8][9][10][11][12][13][14]. In IL, it is often possible to achieve reactions that otherwise proceed only with great difficulty, or even not at all.…”

Section: Introductionmentioning

confidence: 99%

Alkylation of ambident indole anion in ionic liquids

et al. 2007

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“…Moreover, chiral ionic liquids bear the potential of chiral discrimination capabilities in the various analytical and separation methods 5 , such as chromatography, electrophoresis…”

Section: -3mentioning

confidence: 99%

Chiral pyrrolidinium salts derived from menthol as precursor – synthesis and properties

Januś

Gano

2017

Polish Journal of Chemical Technology

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Six new chiral pyrolidinium salts with chiral substituent at quaternary nitrogen atom were synthesized with high overall yields from (-)-menthol as cheap chiral precursor and were identifi ed by NMR and HRMS spectroscopy. It was shown that anion type had the effect on chemical shift of protons adjacent to quaternary nitrogen atom and physical properties of these salts. Salts with NTf 2 or NPf 2 were in a liquid state at room temperature and characterized with the highest thermal stability among others. Furthermore, chiral ionic liquid with NTf 2 anion was used as solvent in Diels-Alder reaction and gave higher yield and stereoselectivity than in ionic liquids with achiral cations. Synthesized chiral salts have the potential as chiral solvents in synthesis and auxiliaries in analytical methods to improve chiral recognition.

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“…[3] As ILs have attracted a lot of attention recently as a new class of solvents, [8] the incorporation of chiral information in these media has caught the interest of several groups. [9] Although details of the structure and dynamics of these solvents as well their interactions with dissolved substances remain largely elusive, chiral ILs have already started to emerge for various purposes [9] including asymmetric synthesis. [10] Very recently, Vo-Thanh and co-workers reported the largest presently known asymmetric induction caused by a chiral IL as the only source of chirality in an asymmetric reaction.…”

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confidence: 99%