Rhodium-catalyzed addition-cyclization reactions of 5-yn-1-ones with arylboronic acids

Tomoya Miura; Masahiko Shimada; Masahiro Murakami

doi:10.1055/s-2005-863718

Rhodium-catalyzed addition-cyclization reactions of 5-yn-1-ones with arylboronic acids

Tomoya Miura, Masahiko Shimada, Masahiro Murakami

Research output: Contribution to journal › Article › peer-review

10 Citations (Scopus)

Abstract

5-Yn-1-ones react with arylboronic acids in the presence of a catalytic amount of rhodium(I) complex having a diolefin ligand to afford 2-alkylidenecyclopentanols through the regioselective addition of an arylrhodium(I) species across the carbon-carbon triple bond, followed by intramolecular nucleophilic addition of the resulting vinylrhodium(I) species to the carbonyl group.

Original language	English
Pages (from-to)	667-669
Number of pages	3
Journal	Synlett
Issue number	4
DOIs	https://doi.org/10.1055/s-2005-863718
Publication status	Published - Mar 4 2005
Externally published	Yes

Keywords

5-Yn-1-one
Addition-cyclization reaction
Arylboronic acid
Nucleophilic addition
Rhodium

ASJC Scopus subject areas

Organic Chemistry

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10.1055/s-2005-863718

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abstract = "5-Yn-1-ones react with arylboronic acids in the presence of a catalytic amount of rhodium(I) complex having a diolefin ligand to afford 2-alkylidenecyclopentanols through the regioselective addition of an arylrhodium(I) species across the carbon-carbon triple bond, followed by intramolecular nucleophilic addition of the resulting vinylrhodium(I) species to the carbonyl group.",

keywords = "5-Yn-1-one, Addition-cyclization reaction, Arylboronic acid, Nucleophilic addition, Rhodium",

author = "Tomoya Miura and Masahiko Shimada and Masahiro Murakami",

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doi = "10.1055/s-2005-863718",

language = "English",

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journal = "Synlett",

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T1 - Rhodium-catalyzed addition-cyclization reactions of 5-yn-1-ones with arylboronic acids

AU - Miura, Tomoya

AU - Shimada, Masahiko

AU - Murakami, Masahiro

PY - 2005/3/4

Y1 - 2005/3/4

N2 - 5-Yn-1-ones react with arylboronic acids in the presence of a catalytic amount of rhodium(I) complex having a diolefin ligand to afford 2-alkylidenecyclopentanols through the regioselective addition of an arylrhodium(I) species across the carbon-carbon triple bond, followed by intramolecular nucleophilic addition of the resulting vinylrhodium(I) species to the carbonyl group.

AB - 5-Yn-1-ones react with arylboronic acids in the presence of a catalytic amount of rhodium(I) complex having a diolefin ligand to afford 2-alkylidenecyclopentanols through the regioselective addition of an arylrhodium(I) species across the carbon-carbon triple bond, followed by intramolecular nucleophilic addition of the resulting vinylrhodium(I) species to the carbonyl group.

KW - 5-Yn-1-one

KW - Addition-cyclization reaction

KW - Arylboronic acid

KW - Nucleophilic addition

KW - Rhodium

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JO - Synlett

JF - Synlett

IS - 4

ER -

Rhodium-catalyzed addition-cyclization reactions of 5-yn-1-ones with arylboronic acids

Abstract

Keywords

ASJC Scopus subject areas

Access to Document

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