Development of L-proline-based Chiral Ionic Liquids for asymmetric Michael Reaction

Karolina Zalewska; Isabel Pinto; Luís Cabrita; Malgorzata E. Zakrzewska; João P. Noronha; M. Nunes da Ponte; Luís C. Branco

doi:10.3390/catal13020270

Development of L-proline-based Chiral Ionic Liquids for asymmetric Michael Reaction

Karolina Zalewska, Isabel Pinto, Luís Cabrita, Malgorzata E. Zakrzewska, João P. Noronha, M. Nunes da Ponte, Luís C. Branco

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Abstract

Different Chiral Ionic Liquids (CIL) based on L-proline have been developed. Simple and efficient synthetic methodologies are used, allowing preparation in good yields for twelve novel CILs using L-proline as a cation or anion combined with suitable counter-ions. A detailed physical and chemical characterization of the CILs was performed to evaluate the influence of counter-ions on the final properties. The most promissory CILs were tested as efficient chiral catalysts in IL media for asymmetric Michael addition reactions of ketones and aldehydes to nitro-olefins. Similar or even better conversions and enantioselectivities (ee up to 95%) compared to the original L-proline were achieved. Additionally, a good product extraction performance using supercritical CO₂ processes was obtained.

Original language	English
Article number	270
Number of pages	16
Journal	Catalysts
Volume	13
DOIs	https://doi.org/10.3390/catal13020270
Publication status	Published - 25 Jan 2023

Keywords

asymmetric Michael reaction
chiral ionic liquids
L-proline
supercritical CO extraction

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Development of L-Proline-Based Chiral Ionic Liquids forFinal published version, 1.7 MBLicence: CC BY

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title = "Development of L-proline-based Chiral Ionic Liquids for asymmetric Michael Reaction",

abstract = "Different Chiral Ionic Liquids (CIL) based on L-proline have been developed. Simple and efficient synthetic methodologies are used, allowing preparation in good yields for twelve novel CILs using L-proline as a cation or anion combined with suitable counter-ions. A detailed physical and chemical characterization of the CILs was performed to evaluate the influence of counter-ions on the final properties. The most promissory CILs were tested as efficient chiral catalysts in IL media for asymmetric Michael addition reactions of ketones and aldehydes to nitro-olefins. Similar or even better conversions and enantioselectivities (ee up to 95%) compared to the original L-proline were achieved. Additionally, a good product extraction performance using supercritical CO2 processes was obtained.",

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author = "Karolina Zalewska and Isabel Pinto and Lu{\'i}s Cabrita and Zakrzewska, {Malgorzata E.} and Noronha, {Jo{\~a}o P.} and {Nunes da Ponte}, M. and Branco, {Lu{\'i}s C.}",

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AU - Zalewska, Karolina

AU - Pinto, Isabel

AU - Cabrita, Luís

AU - Zakrzewska, Malgorzata E.

AU - Noronha, João P.

AU - Nunes da Ponte, M.

AU - Branco, Luís C.

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PY - 2023/1/25

Y1 - 2023/1/25

N2 - Different Chiral Ionic Liquids (CIL) based on L-proline have been developed. Simple and efficient synthetic methodologies are used, allowing preparation in good yields for twelve novel CILs using L-proline as a cation or anion combined with suitable counter-ions. A detailed physical and chemical characterization of the CILs was performed to evaluate the influence of counter-ions on the final properties. The most promissory CILs were tested as efficient chiral catalysts in IL media for asymmetric Michael addition reactions of ketones and aldehydes to nitro-olefins. Similar or even better conversions and enantioselectivities (ee up to 95%) compared to the original L-proline were achieved. Additionally, a good product extraction performance using supercritical CO2 processes was obtained.

AB - Different Chiral Ionic Liquids (CIL) based on L-proline have been developed. Simple and efficient synthetic methodologies are used, allowing preparation in good yields for twelve novel CILs using L-proline as a cation or anion combined with suitable counter-ions. A detailed physical and chemical characterization of the CILs was performed to evaluate the influence of counter-ions on the final properties. The most promissory CILs were tested as efficient chiral catalysts in IL media for asymmetric Michael addition reactions of ketones and aldehydes to nitro-olefins. Similar or even better conversions and enantioselectivities (ee up to 95%) compared to the original L-proline were achieved. Additionally, a good product extraction performance using supercritical CO2 processes was obtained.

KW - asymmetric Michael reaction

KW - chiral ionic liquids

KW - L-proline

KW - supercritical CO extraction

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Development of L-proline-based Chiral Ionic Liquids for asymmetric Michael Reaction

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