Stereoselective iodocyclopropanation of terminal alkenes with iodoform, chromium(II) chloride, and N,N,N',N'-tetraethylethylenediamine.

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.