Stereoselective Iodocyclopropanation of Terminal Alkenes with Iodoform, Chromium(II) Chloride, and N,N,N′,N′-Tetraethylethylenediamine

Kazuhiko Takai, Shota Toshikawa, Atsushi Inoue, Ryo Kokumai

Research output: Contribution to journalArticle

30 Citations (Scopus)

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.

Original languageEnglish
Pages (from-to)12990-12991
Number of pages2
JournalJournal of the American Chemical Society
Volume125
Issue number43
DOIs
Publication statusPublished - Oct 29 2003

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Alkenes
Chromium
Ether
Olefins
Chlorides
Ethers
Aldehydes
Amides
Functional groups
Amines
Esters
Alcohols
Molecules
iodoform
chromous chloride

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

Stereoselective Iodocyclopropanation of Terminal Alkenes with Iodoform, Chromium(II) Chloride, and N,N,N′,N′-Tetraethylethylenediamine. / Takai, Kazuhiko; Toshikawa, Shota; Inoue, Atsushi; Kokumai, Ryo.

In: Journal of the American Chemical Society, Vol. 125, No. 43, 29.10.2003, p. 12990-12991.

Research output: Contribution to journalArticle

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