- Syntheses and properties of fluorous quaternary phosphonium salts that bear four ponytails; new candidates for phase transfer catalysts and ionic liquids
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The fluorous tertiary phosphine [Rf6-(CH2) 2]3P [Rfn = CF3(CF2) n-1] and excess PhCH2Br, CH3(CH 2)3OSO2CF3
- Emnet, Charlotte,Weber, Kathleen M.,Vidal, Jose A.,Consorti, Crestina S.,Stuart, Alison M.,Gladysz
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- Ionic transformations in extremely nonpolar fluorous media: Phase transfer catalysis of halide substitution reactions
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Fluorous solutions of alkyl halides R18(CH2) mX (m = 2, 3; X = Cl, Br, I) are inert toward solid or aqueous NaCl, NaBr, and Kl, but halide substitution occurs in the presence of fluorous phosphonium salts (10 mol %, 76-100 °C).
- Consorti, Crestina S.,Jurisch, Markus,Gladysz, John A.
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p. 2309 - 2312
(2008/02/05)
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- Combining lipase-catalyzed enantiomer-selective acylation with fluorous phase labeling: A new method for the resolution of racemic alcohols
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Lipase-catalyzed acylation of racemic alcohols with a highly fluorinated acyl donor allows their kinetic resolution accompanied by the simultaneous enantiomer-selective fluorous phase labeling. Both the tagged and the untagged enantiomer can be separated without chromatography by a very efficient partition between a fluorous and an organic phase. The method has been successfully applied to the resolution of typically racemic secondary alcohols of low molecular weight. The fluorous label can be recovered quantitatively.
- Hungerhoff, Benno,Sonnenschein, Helmut,Theil, Fritz
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p. 1781 - 1785
(2007/10/03)
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- Separation of enantiomers by extraction based on lipase-catalyzed enantiomer-selective fluorous-phase labeling
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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.
- Hungerhoff, Benno,Sonnenschein, Helmut,Theil, Fritz
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p. 2492 - 2494
(2007/10/03)
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