New Mesoporous Silica-Supported Organocatalysts Based on (2<i>S</i>)-(1,2,4-Triazol-3-yl)-Proline: Efficient, Reusable, and Heterogeneous Catalysts for the Asymmetric Aldol Reaction
Novel organocatalytic systems based on the recently developed (<i>S</i>)-proline derivative (2<i>S</i>)-[5-(benzylthio)-4-phenyl-(1,2,4-triazol)-3-yl]-pyrrolidine supported on mesoporous silica were prepared and their efficiency was assessed in the asymmetric aldol reaction....
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doaj-317dbab4f0224ebdbdae1d7f4ca3fb6d2020-11-25T03:52:00ZengMDPI AGMolecules1420-30492020-10-01254532453210.3390/molecules25194532New Mesoporous Silica-Supported Organocatalysts Based on (2<i>S</i>)-(1,2,4-Triazol-3-yl)-Proline: Efficient, Reusable, and Heterogeneous Catalysts for the Asymmetric Aldol ReactionOmar Sánchez-Antonio0Kevin A. Romero-Sedglach1Erika C. Vázquez-Orta2Eusebio Juaristi3Departamento de Química, Centro de Investigación y de Estudios Avanzados, Avenida IPN # 2508, 07360 Ciudad de México, MexicoDepartamento de Química, Centro de Investigación y de Estudios Avanzados, Avenida IPN # 2508, 07360 Ciudad de México, MexicoDepartamento de Química, Centro de Investigación y de Estudios Avanzados, Avenida IPN # 2508, 07360 Ciudad de México, MexicoDepartamento de Química, Centro de Investigación y de Estudios Avanzados, Avenida IPN # 2508, 07360 Ciudad de México, MexicoNovel organocatalytic systems based on the recently developed (<i>S</i>)-proline derivative (2<i>S</i>)-[5-(benzylthio)-4-phenyl-(1,2,4-triazol)-3-yl]-pyrrolidine supported on mesoporous silica were prepared and their efficiency was assessed in the asymmetric aldol reaction. These materials were fully characterized by FT-IR, MS, XRD, and SEM microscopy, gathering relevant information regarding composition, morphology, and organocatalyst distribution in the doped silica. Careful optimization of the reaction conditions required for their application as catalysts in asymmetric aldol reactions between ketones and aldehydes afforded the anticipated aldol products with excellent yields and moderate diastereo- and enantioselectivities. The recommended experimental protocol is simple, fast, and efficient providing the enantioenriched aldol product, usually without the need of a special work-up or purification protocol. This approach constitutes a remarkable improvement in the field of heterogeneous (<i>S</i>)-proline-based organocatalysis; in particular, the solid-phase silica-bonded catalytic systems described herein allow for a substantial reduction in solvent usage. Furthermore, the supported system described here can be recovered, reactivated, and reused several times with limited loss in catalytic efficiency relative to freshly synthesized organocatalysts.https://www.mdpi.com/1420-3049/25/19/4532(S)-prolinesupported organocatalystsasymmetric aldol reactionreusable organocatalysts |
collection |
DOAJ |
language |
English |
format |
Article |
sources |
DOAJ |
author |
Omar Sánchez-Antonio Kevin A. Romero-Sedglach Erika C. Vázquez-Orta Eusebio Juaristi |
spellingShingle |
Omar Sánchez-Antonio Kevin A. Romero-Sedglach Erika C. Vázquez-Orta Eusebio Juaristi New Mesoporous Silica-Supported Organocatalysts Based on (2<i>S</i>)-(1,2,4-Triazol-3-yl)-Proline: Efficient, Reusable, and Heterogeneous Catalysts for the Asymmetric Aldol Reaction Molecules (S)-proline supported organocatalysts asymmetric aldol reaction reusable organocatalysts |
author_facet |
Omar Sánchez-Antonio Kevin A. Romero-Sedglach Erika C. Vázquez-Orta Eusebio Juaristi |
author_sort |
Omar Sánchez-Antonio |
title |
New Mesoporous Silica-Supported Organocatalysts Based on (2<i>S</i>)-(1,2,4-Triazol-3-yl)-Proline: Efficient, Reusable, and Heterogeneous Catalysts for the Asymmetric Aldol Reaction |
title_short |
New Mesoporous Silica-Supported Organocatalysts Based on (2<i>S</i>)-(1,2,4-Triazol-3-yl)-Proline: Efficient, Reusable, and Heterogeneous Catalysts for the Asymmetric Aldol Reaction |
title_full |
New Mesoporous Silica-Supported Organocatalysts Based on (2<i>S</i>)-(1,2,4-Triazol-3-yl)-Proline: Efficient, Reusable, and Heterogeneous Catalysts for the Asymmetric Aldol Reaction |
title_fullStr |
New Mesoporous Silica-Supported Organocatalysts Based on (2<i>S</i>)-(1,2,4-Triazol-3-yl)-Proline: Efficient, Reusable, and Heterogeneous Catalysts for the Asymmetric Aldol Reaction |
title_full_unstemmed |
New Mesoporous Silica-Supported Organocatalysts Based on (2<i>S</i>)-(1,2,4-Triazol-3-yl)-Proline: Efficient, Reusable, and Heterogeneous Catalysts for the Asymmetric Aldol Reaction |
title_sort |
new mesoporous silica-supported organocatalysts based on (2<i>s</i>)-(1,2,4-triazol-3-yl)-proline: efficient, reusable, and heterogeneous catalysts for the asymmetric aldol reaction |
publisher |
MDPI AG |
series |
Molecules |
issn |
1420-3049 |
publishDate |
2020-10-01 |
description |
Novel organocatalytic systems based on the recently developed (<i>S</i>)-proline derivative (2<i>S</i>)-[5-(benzylthio)-4-phenyl-(1,2,4-triazol)-3-yl]-pyrrolidine supported on mesoporous silica were prepared and their efficiency was assessed in the asymmetric aldol reaction. These materials were fully characterized by FT-IR, MS, XRD, and SEM microscopy, gathering relevant information regarding composition, morphology, and organocatalyst distribution in the doped silica. Careful optimization of the reaction conditions required for their application as catalysts in asymmetric aldol reactions between ketones and aldehydes afforded the anticipated aldol products with excellent yields and moderate diastereo- and enantioselectivities. The recommended experimental protocol is simple, fast, and efficient providing the enantioenriched aldol product, usually without the need of a special work-up or purification protocol. This approach constitutes a remarkable improvement in the field of heterogeneous (<i>S</i>)-proline-based organocatalysis; in particular, the solid-phase silica-bonded catalytic systems described herein allow for a substantial reduction in solvent usage. Furthermore, the supported system described here can be recovered, reactivated, and reused several times with limited loss in catalytic efficiency relative to freshly synthesized organocatalysts. |
topic |
(S)-proline supported organocatalysts asymmetric aldol reaction reusable organocatalysts |
url |
https://www.mdpi.com/1420-3049/25/19/4532 |
work_keys_str_mv |
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