The electronic effect of ligands on stereoselectivity in the rhodium(I)-catalyzed asymmetric Pauson-Khand-type reaction under a carbon monoxide atmosphere

Dong Eun Kim; Choong Choi; In Su Kim; Séverine Jeulin; Virginie Ratovelomanana-Vidal; Jean Pierre Genêt; Nakcheol Jeong

doi:10.1055/s-2006-950369

The electronic effect of ligands on stereoselectivity in the rhodium(I)-catalyzed asymmetric Pauson-Khand-type reaction under a carbon monoxide atmosphere

Dong Eun Kim, Choong Choi, In Su Kim, Séverine Jeulin, Virginie Ratovelomanana-Vidal, Jean Pierre Genêt, Nakcheol Jeong

Department of Chemistry

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

19 Citations (Scopus)

Abstract

Based on the proposed mechanism, the electronic effects of various ligands on the stereoselectivity and reaction rate of the rhodium(I)-catalyzed asymmetric Pauson-Khand-type reaction were examined. We demonstrated that both the reaction rate and the enantioselectivity are significantly dependent on the electron density of the ligands; when ligands bearing deshielded phosphine were utilized, the reaction rate was slower, but the products were obtained with improved enantioselectivity.

Original language	English
Pages (from-to)	4053-4059
Number of pages	7
Journal	Synthesis
Issue number	23
DOIs	https://doi.org/10.1055/s-2006-950369
Publication status	Published - 2006 Dec 1

Keywords

Asymmetric catalysts
Atropisomeric ligands
BINAP ligands
Electronic effects
Pauson-Khand reaction

ASJC Scopus subject areas

Catalysis
Organic Chemistry

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The electronic effect of ligands on stereoselectivity in the rhodium(I)-catalyzed asymmetric Pauson-Khand-type reaction under a carbon monoxide atmosphere. / Kim, Dong Eun; Choi, Choong; Kim, In Su; Jeulin, Séverine; Ratovelomanana-Vidal, Virginie; Genêt, Jean Pierre; Jeong, Nakcheol.

In: Synthesis, No. 23, 01.12.2006, p. 4053-4059.

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

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AU - Kim, In Su

AU - Jeulin, Séverine

AU - Ratovelomanana-Vidal, Virginie

AU - Genêt, Jean Pierre

AU - Jeong, Nakcheol

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N2 - Based on the proposed mechanism, the electronic effects of various ligands on the stereoselectivity and reaction rate of the rhodium(I)-catalyzed asymmetric Pauson-Khand-type reaction were examined. We demonstrated that both the reaction rate and the enantioselectivity are significantly dependent on the electron density of the ligands; when ligands bearing deshielded phosphine were utilized, the reaction rate was slower, but the products were obtained with improved enantioselectivity.

AB - Based on the proposed mechanism, the electronic effects of various ligands on the stereoselectivity and reaction rate of the rhodium(I)-catalyzed asymmetric Pauson-Khand-type reaction were examined. We demonstrated that both the reaction rate and the enantioselectivity are significantly dependent on the electron density of the ligands; when ligands bearing deshielded phosphine were utilized, the reaction rate was slower, but the products were obtained with improved enantioselectivity.

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KW - Atropisomeric ligands

KW - BINAP ligands

KW - Electronic effects

KW - Pauson-Khand reaction

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The electronic effect of ligands on stereoselectivity in the rhodium(I)-catalyzed asymmetric Pauson-Khand-type reaction under a carbon monoxide atmosphere

Abstract

Keywords

ASJC Scopus subject areas

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