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New Mesoporous Silica-Supported Organocatalysts Based on (2S)-(1,2,4-Triazol-3-yl)-Proline: Efficient, Reusable, and Heterogeneous Catalysts for the Asymmetric Aldol Reaction.
Molecules. 2020 Oct 03; 25(19)M

Abstract

Novel organocatalytic systems based on the recently developed (S)-proline derivative (2S)-[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 (S)-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.

Authors+Show Affiliations

Departamento de Química, Centro de Investigación y de Estudios Avanzados, Avenida IPN # 2508, 07360 Ciudad de México, Mexico.Departamento de Química, Centro de Investigación y de Estudios Avanzados, Avenida IPN # 2508, 07360 Ciudad de México, Mexico.Departamento de Química, Centro de Investigación y de Estudios Avanzados, Avenida IPN # 2508, 07360 Ciudad de México, Mexico.Departamento de Química, Centro de Investigación y de Estudios Avanzados, Avenida IPN # 2508, 07360 Ciudad de México, Mexico. El Colegio Nacional, Luis González Obregón # 23, Centro Histórico, 06020 Ciudad de México, Mexico.

Pub Type(s)

Journal Article

Language

eng

PubMed ID

33022926

Citation

Sánchez-Antonio, Omar, et al. "New Mesoporous Silica-Supported Organocatalysts Based On (2S)-(1,2,4-Triazol-3-yl)-Proline: Efficient, Reusable, and Heterogeneous Catalysts for the Asymmetric Aldol Reaction." Molecules (Basel, Switzerland), vol. 25, no. 19, 2020.
Sánchez-Antonio O, Romero-Sedglach KA, Vázquez-Orta EC, et al. New Mesoporous Silica-Supported Organocatalysts Based on (2S)-(1,2,4-Triazol-3-yl)-Proline: Efficient, Reusable, and Heterogeneous Catalysts for the Asymmetric Aldol Reaction. Molecules. 2020;25(19).
Sánchez-Antonio, O., Romero-Sedglach, K. A., Vázquez-Orta, E. C., & Juaristi, E. (2020). New Mesoporous Silica-Supported Organocatalysts Based on (2S)-(1,2,4-Triazol-3-yl)-Proline: Efficient, Reusable, and Heterogeneous Catalysts for the Asymmetric Aldol Reaction. Molecules (Basel, Switzerland), 25(19). https://doi.org/10.3390/molecules25194532
Sánchez-Antonio O, et al. New Mesoporous Silica-Supported Organocatalysts Based On (2S)-(1,2,4-Triazol-3-yl)-Proline: Efficient, Reusable, and Heterogeneous Catalysts for the Asymmetric Aldol Reaction. Molecules. 2020 Oct 3;25(19) PubMed PMID: 33022926.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - New Mesoporous Silica-Supported Organocatalysts Based on (2S)-(1,2,4-Triazol-3-yl)-Proline: Efficient, Reusable, and Heterogeneous Catalysts for the Asymmetric Aldol Reaction. AU - Sánchez-Antonio,Omar, AU - Romero-Sedglach,Kevin A, AU - Vázquez-Orta,Erika C, AU - Juaristi,Eusebio, Y1 - 2020/10/03/ PY - 2020/09/16/received PY - 2020/09/30/revised PY - 2020/10/01/accepted PY - 2020/10/7/entrez PY - 2020/10/8/pubmed PY - 2021/3/20/medline KW - (S)-proline KW - asymmetric aldol reaction KW - reusable organocatalysts KW - supported organocatalysts JF - Molecules (Basel, Switzerland) JO - Molecules VL - 25 IS - 19 N2 - Novel organocatalytic systems based on the recently developed (S)-proline derivative (2S)-[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 (S)-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. SN - 1420-3049 UR - https://www.unboundmedicine.com/medline/citation/33022926/New_Mesoporous_Silica_Supported_Organocatalysts_Based_on__2S___124_Triazol_3_yl__Proline:_Efficient_Reusable_and_Heterogeneous_Catalysts_for_the_Asymmetric_Aldol_Reaction_ DB - PRIME DP - Unbound Medicine ER -