Separation of Enantiomers by Extraction Based on Lipase-Catalyzed Enantiomer-Selective Fluorous-Phase Labeling

Abstract

No chromatography is necessary to separate a racemic alcohol into its enantiomers. A highly fluorinated acyl residue was tranferred in an enantiomer‐selective manner onto a racemic alcohol in the presence of a lipase [Eq. (1)]. The labeled enantiomer was separated from the unlabeled one by a simple but very efficient partition between fluorous and organic phases.

Process intensification with biocatalysts: dynamic kinetic resolution and fluorous phase switch with continuous extraction

“…Theil and co-workers developed a new acylation reagent, trifluoroethyl-1H,1H,2H,2H-perfluoroundecanoate [45][46][47], and demonstrated its compatibility with lipase-catalyzed transesterifications. Compounds that had been tagged with this fluorous 'ponytail' could be easily extracted into a fluorous solvent (perfluorohexane; FC-72).…”

Metal Extraction from Water and Organic Solvents into Fluorous Solvents by Fluorinated β-Diketone and Its Application to the Colorimetric Analysis of Metal Ions

“…Due to their remarkable solvent properties, fluorous biphasic and triphasic systems have been extensively investigated for organic synthesis 2,4-9 and enzymatic reactions. [10][11][12][13] Since the solubility of fluorous solvents in water is extremely low and similar to but generally lower than conventional organic solvents, fluorous solvents are likely to be potential candidates for novel separation media in metal extraction. Since fluorous solvents are immiscible with organic solvents, metal ions dissolved in organic solvents in the form of organometallic catalysts or impurities could be removed by fluorous solvents without using water.…”

Perfluorocarbon-based Liquid-Liquid Extraction for Separation of Transition Metal Ions

“…Remarkable progress on fluorous solvents has highlighted fluorocarbons, especially perfluorinated alkanes and ethers, as reaction and separation media. [1][2][3][4][5][6][7][8][9][10] Water solubility in perfluorocarbons is extremely low. Perfluorocarbons are usually immiscible with non-fluorinated organic solvents at ambient temperature.…”

“…1-3 Since Zhu reported organic reactions in perfluorocarbons, several research groups have demonstrated the feasibility of fluorous solvents as alternative reaction and separation media to conventional organic solvents. [4][5][6][7][8] The fluorous biphasic system developed by Horvath and Rabai offers elegant integration of a homogeneous reaction and subsequent separation using a fluorous tag.…”

“…[1][2][3] Since Zhu reported organic reactions in perfluorocarbons, several research groups have demonstrated the feasibility of fluorous solvents as alternative reaction and separation media to conventional organic solvents. [4][5][6][7][8] The fluorous biphasic system developed by Horvath and Rabai offers elegant integration of a homogeneous reaction and subsequent separation using a fluorous tag. 1 Despite the outstanding studies on the separation of organic compounds based on fluorous multiphase systems, [1][2][3][11][12][13] there are few reports on the extraction of metal ions using perfluorocarbons.…”