Stereoselective iodocyclopropanation of terminal alkenes with iodoform, chromium(II) chloride, and N,N,N',N'-tetraethylethylenediamine |
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Authors: | Takai Kazuhiko Toshikawa Shota Inoue Atsushi Kokumai Ryo |
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Institution: | Department of Applied Chemistry, Faculty of Engineering, Okayama University, Tsushima, Okayama 700-8530, Japan. ktakai@cc.okayama-u.ac.jp |
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Abstract: | Chemoselectivity of a reagent for (E)-olefination of aldehydes derived by reduction of iodoform with chromium(II) chloride in THF changes markedly by addition of TEEDA (N,N,N',N'-tetraethylethylenediamine), and trans-iodocyclopropanes are produced stereoselectively from terminal alkenes by treatment with the base-added reagent system. The iodocyclopropanation occurs only at terminal double bonds, and di- and trisubstituted double bonds in the same molecules remained unchanged. Such functional groups as alcohol, ether, silyl ether, ester, tertiary amine, and amide groups are compatible with the reaction conditions. |
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