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Reduction of Carbonyl Compounds by Lanthanide Metal/2-Propanol: In-situ Generation of Samarium Isopropyloxide for Stereoselective Meerwein-Ponndorf-Verley Reduction

Shin-ichi Fukuzawa*, Narihito Nakano, Takahide Saitoh

*Department of Applied Chemistry, Institute of Science and Engineering, Chuo University, 1-13-27 Kasuga, Bunkyo-ku, Tokyo 112-8551, Japan, Email:

S.-I. Fukuzawa, N. Nakano, T. Saitoh, Eur. J. Org. Chem., 2004, 2863-2867.

DOI: 10.1002/ejoc.200400030


The reduction of ketones and aldehydes with lanthanide metals (La, Ce, Sm, Yb) and a catalytic amount of iodine (5 mol %) in iPrOH proceeded smoothly to produce the corresponding alcohols as the major products in good yield, while in THF, methanol, and ethanol the pinacols were mainly produced. The yields of alcohols were improved most effectively by the use of Sm metal.

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proposed mechanism

Key Words

Lanthanides, Meerwein-Ponndorf-Verley reduction, Reductions, Samarium, Samarium alkoxide, Isopropanol

ID: J24-Y2004-540