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CBS Reductions with a Fluorous Prolinol Immobilized in a Hydrofluoroether Solvent

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journal contribution
posted on 06.03.2008, 00:00 by Qianli Chu, Marvin S. Yu, Dennis P. Curran
A fluorous prolinol precatalyst bearing only 34 fluorine atoms has been immobilized in the hydrofluoroether solvent HFE-7500. The CBS reduction of acetophenone proceeded rapidly, in high yield and in high ee in the absence of any organic solvent. The organic product was stripped from the HFE-7500 phase with a polar solvent, and the HFE-7500 phase was reused “as is” with satisfactory results through eight runs. This process is an attractive prototype for the large-scale use, recovery, and reuse of fluorous organocatalysts.