CBS reductions with a fluorous prolinol immobilized in a hydrofluoroether solvent.
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.
Chu
Qianli
Q
Fluorous Technologies, Inc., UPARC, 970 William Pitt Way, Pittsburgh, Pennsylvania 15238, USA.
Yu
Marvin S
MS
Curran
Dennis P
DP
D020650:Combinatorial Chemistry Techniques; D004987:Ethers / Q000737:chemistry*; D017611:Fluorine Compounds / Q000737:chemistry*; D015394:Molecular Structure; D010084:Oxidation-Reduction; D011759:Pyrrolidines / Q000737:chemistry*; D012997:Solvents
D004987:Ethers; D017611:Fluorine Compounds; C472825:HFE-7500; D011759:Pyrrolidines; D012997:Solvents; C010509:prolinol