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Stereospecific and Stereoselective Preparation of 2-(1-Hydroxyalkyl)-1-alkylcyclopropanols from α,β-Epoxy Ketones and Bis(iodozincio)methane

Kenichi Nomura, Koichiro Oshima, Seijiro Matsubara*

*Department of Material Chemistry, Graduate School of Engineering, Kyoto University, Kyoutodaigaku-Katsura, Nishikyo, Kyoto, Email:

K. Nomura, K. Oshima, S. Matsubara, Angew. Chem. Int. Ed., 2005, 44, 5860-5863.

DOI: 10.1002/anie.200501644


A diastereofacial selective attack of epoxy ketones by bis(iodozincio)methane leads to 2-(1-hydroxyalkyl)-1-alkylcyclopropanols in good yields. The dizinc reagent, which acts as an effective bidentate Lewis acid, is easily prepared from diiodomethane and zinc powder.

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Key Words

diastereoselectivity, epoxy ketones, small ring systems, cyclopropanols, zinc

ID: J06-Y2005-1410