Stereoselective synthesis of α-allenols by rhodium-catalyzed reaction of alkynyl oxiranes with arylboronic acids

Tomoya Miura; Masahiko Shimada; Sung Yu Ku; Tomohiro Tamai; Masahiro Murakami

doi:10.1002/anie.200701505

Stereoselective synthesis of α-allenols by rhodium-catalyzed reaction of alkynyl oxiranes with arylboronic acids

Tomoya Miura, Masahiko Shimada, Sung Yu Ku, Tomohiro Tamai, Masahiro Murakami

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

76 Citations (Scopus)

Abstract

(Chemical Equation Presented) Better than Cu, Pd, and Fe catalysts: The rhodium-catalyzed reaction of alkynyl oxiranes with arylboronic acids provides synconfigured α-allenols with excellent diastereoselectivity. Precoordination of the oxygen atom of the oxirane ring to rhodium is assumed to contribute to the high stereoselectivity as well as high reactivity.

Original language	English
Pages (from-to)	7101-7103
Number of pages	3
Journal	Angewandte Chemie - International Edition
Volume	46
Issue number	37
DOIs	https://doi.org/10.1002/anie.200701505
Publication status	Published - 2007
Externally published	Yes

Keywords

Addition
Allenes
Boron
Rhodium
β-oxygen elimination

ASJC Scopus subject areas

Catalysis
Chemistry(all)

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10.1002/anie.200701505

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author = "Tomoya Miura and Masahiko Shimada and Ku, {Sung Yu} and Tomohiro Tamai and Masahiro Murakami",

year = "2007",

doi = "10.1002/anie.200701505",

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AU - Miura, Tomoya

AU - Shimada, Masahiko

AU - Ku, Sung Yu

AU - Tamai, Tomohiro

AU - Murakami, Masahiro

PY - 2007

Y1 - 2007

N2 - (Chemical Equation Presented) Better than Cu, Pd, and Fe catalysts: The rhodium-catalyzed reaction of alkynyl oxiranes with arylboronic acids provides synconfigured α-allenols with excellent diastereoselectivity. Precoordination of the oxygen atom of the oxirane ring to rhodium is assumed to contribute to the high stereoselectivity as well as high reactivity.

AB - (Chemical Equation Presented) Better than Cu, Pd, and Fe catalysts: The rhodium-catalyzed reaction of alkynyl oxiranes with arylboronic acids provides synconfigured α-allenols with excellent diastereoselectivity. Precoordination of the oxygen atom of the oxirane ring to rhodium is assumed to contribute to the high stereoselectivity as well as high reactivity.

KW - Addition

KW - Allenes

KW - Boron

KW - Rhodium

KW - β-oxygen elimination

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JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

IS - 37

ER -

Stereoselective synthesis of α-allenols by rhodium-catalyzed reaction of alkynyl oxiranes with arylboronic acids

Abstract

Keywords

ASJC Scopus subject areas

Access to Document

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