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DOI: 10.1055/s-2007-1000879
Nonenzymatic Kinetic Resolution of Amines in Ionic Liquids [1]
Publication History
Publication Date:
04 January 2008 (online)
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Abstract
Ionic liquids are remarkably suitable and clean media for performing nonenzymatic kinetic resolution (KR) of amines through enantioselective N-acetylation: high levels of selectivity were obtained with a large variety of amines at room temperature (up to s = 30).
Key words
kinetic resolution - amines - ionic liquids - nonenzymatic
Charles Mioskowski (1946-2007).
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References and Notes
Charles Mioskowski (1946-2007).
2Present address: Laboratoire de Chimie Organique, CNRS, ESPCI, 10 rue Vauquelin, 75231 Paris Cedex 05, France.
22General Procedure: The racemic amine (0.24 mmol) was added to a stirred solution of (1S,2S)-2 (50 mg, 0.12 mmol) in the chosen ionic liquid at the selected temperature. The reaction mixture was stirred at the same temperature until complete conversion of the acetylating agent [reaction followed by TLC analysis (EtOAc-n-hexane, 2:8)]. Once complete conversion of the reagent was observed, H2O and EtOAc were added and the two phases were separated. The organic phase was dried over MgSO4 and evaporated under reduced pressure. The resulting residue was purified by flash chromatography on silica gel (EtOAc-hexane, 1:1), and the enantiomeric excess was determined by HPLC on a chiral stationary phase.
23The counterion (Cl-, NTf2 -, etc.) confers the basic character to the ionic liquids.
24The equilibrium could be displaced in an enantioselective fashion by the acid-free sulfonamide.