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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 (free Supporting Information)


 

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 FeCl24H2O or CuCl22H2O 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


ID: J42-Y2015