The Stereoselective Reductions of Ketones to the Most Thermodynamically Stable Alcohols Using Lithium and Hydrated Salts of Common Transition Metals

Nicole Kennedy* and Theodore Cohen*

*Department of Chemistry, University of Pittsburgh, Pittsburgh, Pennsylvania 15260, United States, Email: nmk28pitt.edu, cohenpitt.edu

N. Kennedy, T. Cohen, J. Org. Chem., 2015, 80, 8134-8141.

DOI: 10.1021/acs.joc.5b01232

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Abstract

For highly stereoselective reductions of a large number of five- and six-membered cyclic ketones to the most thermodynamically stable alcohols, ketones are treated with lithium dispersion and either FeCl₂·4H₂O or CuCl₂·2H₂O in THF at room temperature. This protocol is more convenient and efficient than those commonly reported for similar reductions.

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Key Words

reduction of carbonyl compounds, cyclohexanols, Iron

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ID: J42-Y2015