Stereoselective Iodocyclopropanation of Terminal Alkenes with Iodoform, Chromium(II) Chloride, and N,N,N‘,N‘-Tetraethylethylenediamine
2003-10-01T00:00:00Z (GMT) by
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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