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