The role of the solvent in the asymmetric hydrogenation of β-keto esters with Ru-BINAP

Adi Wolfson; Ivo F.J. Vankelecom; Shimona Geresh; Pierre A. Jacobs

doi:10.1016/S1381-1169(02)00681-7

The role of the solvent in the asymmetric hydrogenation of β-keto esters with Ru-BINAP

Adi Wolfson, Ivo F.J. Vankelecom, Shimona Geresh, Pierre A. Jacobs

Department of Biotechnology Engineering

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

47 Scopus citations

Abstract

The influence of the solvent on the asymmetric hydrogenation of methyl acetoacetate, as a representative β-keto esters, with Ru-BINAP was studied. The highest activities were measured when the reaction proceeded in methanol, ethanol or isopropanol. These solvents, which also act as proton donors, accelerate product release from the reaction intermediate. The presence of water in the reaction mixture has been found to be detrimental for both activity and enantioselectivity. All results could be explained by the existence of two different solvent dependent reaction pathways for product release.

Original language	English
Pages (from-to)	39-45
Number of pages	7
Journal	Journal of Molecular Catalysis A: Chemical
Volume	198
Issue number	1-2
DOIs	https://doi.org/10.1016/S1381-1169(02)00681-7
State	Published - 1 May 2003

Keywords

Asymmetric hydrogenation
Keto esters
Ru-BINAP
Solvent effect
Transition metal complex

ASJC Scopus subject areas

Catalysis
Process Chemistry and Technology
Physical and Theoretical Chemistry

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10.1016/S1381-1169(02)00681-7

Cite this

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title = "The role of the solvent in the asymmetric hydrogenation of β-keto esters with Ru-BINAP",

abstract = "The influence of the solvent on the asymmetric hydrogenation of methyl acetoacetate, as a representative β-keto esters, with Ru-BINAP was studied. The highest activities were measured when the reaction proceeded in methanol, ethanol or isopropanol. These solvents, which also act as proton donors, accelerate product release from the reaction intermediate. The presence of water in the reaction mixture has been found to be detrimental for both activity and enantioselectivity. All results could be explained by the existence of two different solvent dependent reaction pathways for product release.",

keywords = "Asymmetric hydrogenation, Keto esters, Ru-BINAP, Solvent effect, Transition metal complex",

author = "Adi Wolfson and Vankelecom, {Ivo F.J.} and Shimona Geresh and Jacobs, {Pierre A.}",

note = "Funding Information: AW acknowledges a postdoctoral fellowship in the frame of the IAP-network in supramolecular chemistry and catalysis, sponsored by the Belgian Federal Government. The research is done in the same framework.",

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AU - Wolfson, Adi

AU - Vankelecom, Ivo F.J.

AU - Geresh, Shimona

AU - Jacobs, Pierre A.

N1 - Funding Information: AW acknowledges a postdoctoral fellowship in the frame of the IAP-network in supramolecular chemistry and catalysis, sponsored by the Belgian Federal Government. The research is done in the same framework.

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Y1 - 2003/5/1

N2 - The influence of the solvent on the asymmetric hydrogenation of methyl acetoacetate, as a representative β-keto esters, with Ru-BINAP was studied. The highest activities were measured when the reaction proceeded in methanol, ethanol or isopropanol. These solvents, which also act as proton donors, accelerate product release from the reaction intermediate. The presence of water in the reaction mixture has been found to be detrimental for both activity and enantioselectivity. All results could be explained by the existence of two different solvent dependent reaction pathways for product release.

AB - The influence of the solvent on the asymmetric hydrogenation of methyl acetoacetate, as a representative β-keto esters, with Ru-BINAP was studied. The highest activities were measured when the reaction proceeded in methanol, ethanol or isopropanol. These solvents, which also act as proton donors, accelerate product release from the reaction intermediate. The presence of water in the reaction mixture has been found to be detrimental for both activity and enantioselectivity. All results could be explained by the existence of two different solvent dependent reaction pathways for product release.

KW - Asymmetric hydrogenation

KW - Keto esters

KW - Ru-BINAP

KW - Solvent effect

KW - Transition metal complex

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The role of the solvent in the asymmetric hydrogenation of β-keto esters with Ru-BINAP

Abstract

Keywords

ASJC Scopus subject areas

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