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: matsubar
orgrxn.mbox.media.kyoto-u.ac.jp
K. Nomura, K. Oshima, S. Matsubara, Angew. Chem. Int. Ed., 2005, 44, 5860-5863.
DOI: 10.1002/anie.200501644
Abstract
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
