Chiral Ionic Liquids from Carbohydrates: Synthesis and Properties

Abstract

Due to their particular properties the use of ionic liquids is growing. Because of their chiral discriminated properties chiral ionic liquids synthesized from mono, polysaccharides or cyclodextrins are used as catalysts in asymmetric synthesis, chiral selectors in NMR studies or as stationary phases in chiral chromatographic analysis. Chiral carbohydrate ionic liquids are a recent topic and only few examples in the literature describe applications of ionic liquids derived from monosaccharides. Isomannide and isosorbide are the most explored and demonstrate important features as chiral selectors and as catalysts in asymmetric synthesis. Carbohydrate imidazolium salts have been explored as soluble supports for oligosaccharide synthesis and polymers resulting from carbohydrate ionic liquids polymerization have been reported. Cyclodextrin ionic liquids have been described and the ability to produce inclusion complexes was explored.

Click Reactions as a Key Step for an Efficient and Selective Synthesis of D-Xylose-Based ILs

“…Only a few examples of carbohydrates-based ILs were reported in the literature [50,51,52,53,54,55,56,57] (Figure 2). First, in 2003 Dickenson et al .…”

“…Glucose was also used as starting material for the elaboration of either a new class of chiral solvents from low-cost natural sources [51] or multiphase particles for cosmetic applications [52]. Next, isomanide or isosorbide-based ILs were prepared as solvents for chiral discrimination or asymmetric organic reactions [53,54,55,56,57].…”