Stereoselective Iodine Atom Transfer [3 + 2] Cycloaddition Reaction with Alkenes Using Unsymmetrical Allylated Active Methine Radicals

Osamu Kitagawa, Shinsaku Miyaji, Chiseko Sakuma, Takeo Taguchi

Research output: Contribution to journalArticle

10 Citations (Scopus)

Abstract

Treatment of 1-diethylphosphonyl- or 1-phenyl-sulfonyl-2-(iodomethyl)cyclopropane-l-carboxylate with Et3B leads to an unsymmetrical allylated active methine radical species that gives functionalized cyclopentane derivatives with high stereoselectivity through iodine atom transfer [3 + 2] cycloaddition reaction with alkenes.

Original languageEnglish
Pages (from-to)2607-2610
Number of pages4
JournalJournal of Organic Chemistry
Volume69
Issue number7
DOIs
Publication statusPublished - 2004 Apr 2
Externally publishedYes

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Cyclopentanes
Stereoselectivity
Cycloaddition
Alkenes
Iodine
Derivatives
Atoms
cyclopropane

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Stereoselective Iodine Atom Transfer [3 + 2] Cycloaddition Reaction with Alkenes Using Unsymmetrical Allylated Active Methine Radicals. / Kitagawa, Osamu; Miyaji, Shinsaku; Sakuma, Chiseko; Taguchi, Takeo.

In: Journal of Organic Chemistry, Vol. 69, No. 7, 02.04.2004, p. 2607-2610.

Research output: Contribution to journalArticle

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