ja0373061_si_001.pdf (141.29 kB)
Stereoselective Iodocyclopropanation of Terminal Alkenes with Iodoform, Chromium(II) Chloride, and N,N,N‘,N‘-Tetraethylethylenediamine
journal contribution
posted on 2003-10-01, 00:00 authored by Kazuhiko Takai, Shota Toshikawa, Atsushi Inoue, Ryo KokumaiChemoselectivity 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.
History
Usage metrics
Categories
Keywords
terminal alkenesiodocyclopropanationreaction conditionsstereoselectivelyTerminal Alkenessilyl etherChlorideolefinationchromiumTetraethylethylenediamineTEEDAaldehydeesterSuchamide groupschlorideiodoformTHF changesmoleculetetraethylethylenediaminereagentIodoformtrisubstitutedaminetranChemoselectivityStereoselective IodocyclopropanationChromiumiodocyclopropanebond
Licence
Exports
RefWorks
BibTeX
Ref. manager
Endnote
DataCite
NLM
DC