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

Osamu Kitagawa; Shinsaku Miyaji; Chiseko Sakuma; Takeo Taguchi

doi:10.1021/jo035771a

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 journal › Article › peer-review

11 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 language	English
Pages (from-to)	2607-2610
Number of pages	4
Journal	Journal of Organic Chemistry
Volume	69
Issue number	7
DOIs	https://doi.org/10.1021/jo035771a
Publication status	Published - 2004 Apr 2
Externally published	Yes

ASJC Scopus subject areas

Organic Chemistry

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10.1021/jo035771a

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

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.",

author = "Osamu Kitagawa and Shinsaku Miyaji and Chiseko Sakuma and Takeo Taguchi",

year = "2004",

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doi = "10.1021/jo035771a",

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AU - Kitagawa, Osamu

AU - Miyaji, Shinsaku

AU - Sakuma, Chiseko

AU - Taguchi, Takeo

PY - 2004/4/2

Y1 - 2004/4/2

N2 - 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.

AB - 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.

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U2 - 10.1021/jo035771a

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

Abstract

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