Organic Letters 2008-03-06

CBS reductions with a fluorous prolinol immobilized in a hydrofluoroether solvent.

Qianli Chu, Marvin S Yu, Dennis P Curran

Index: Org. Lett. 10(5) , 749-52, (2008)

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Abstract

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.