Stereoselective Iodocyclopropanation of Terminal Alkenes with Iodoform, Chromium(II) Chloride, and <i>N</i>,<i>N</i>,<i>N</i>‘,<i>N</i>‘-Tetraethylethylenediamine Kazuhiko Takai Shota Toshikawa Atsushi Inoue Ryo Kokumai 10.1021/ja0373061.s001 https://acs.figshare.com/articles/journal_contribution/Stereoselective_Iodocyclopropanation_of_Terminal_Alkenes_with_Iodoform_Chromium_II_Chloride_and_i_N_i_i_N_i_i_N_i_i_N_i_-Tetraethylethylenediamine/3655287 Chemoselectivity of a reagent for (<i>E</i>)-olefination of aldehydes derived by reduction of iodoform with chromium(II) chloride in THF changes markedly by addition of TEEDA (<i>N</i>,<i>N</i>,<i>N</i>‘,<i>N</i>‘-tetraethylethylenediamine), and <i>trans</i>-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. 2003-10-01 00:00:00 terminal alkenes iodocyclopropanation reaction conditions stereoselectively Terminal Alkenes silyl ether Chloride olefination chromium Tetraethylethylenediamine TEEDA aldehyde ester Such amide groups chloride iodoform THF changes molecule tetraethylethylenediamine reagent Iodoform trisubstituted amine tran Chemoselectivity Stereoselective Iodocyclopropanation Chromium iodocyclopropane bond