{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,9,28]],"date-time":"2026-09-28T07:10:21Z","timestamp":1790579421275,"version":"4.1.0"},"reference-count":107,"publisher":"MDPI AG","issue":"19","license":[{"start":{"date-parts":[[2020,10,3]],"date-time":"2020-10-03T00:00:00Z","timestamp":1601683200000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"DOI":"10.13039\/501100003141","name":"Consejo Nacional de Ciencia y Tecnolog\u00eda","doi-asserted-by":"publisher","award":["220945"],"award-info":[{"award-number":["220945"]}],"id":[{"id":"10.13039\/501100003141","id-type":"DOI","asserted-by":"publisher"}]},{"name":"Fund SEP-CINVESTAV","award":["126"],"award-info":[{"award-number":["126"]}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Molecules"],"abstract":"<jats:p>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.<\/jats:p>","DOI":"10.3390\/molecules25194532","type":"journal-article","created":{"date-parts":[[2020,10,3]],"date-time":"2020-10-03T07:22:16Z","timestamp":1601709736000},"page":"4532","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":18,"title":["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"],"prefix":"10.3390","volume":"25","author":[{"ORCID":"https:\/\/orcid.org\/0000-0003-2917-2992","authenticated-orcid":false,"given":"Omar","family":"S\u00e1nchez-Antonio","sequence":"first","affiliation":[{"name":"Departamento de Qu\u00edmica, Centro de Investigaci\u00f3n y de Estudios Avanzados, Avenida IPN # 2508, 07360 Ciudad de M\u00e9xico, Mexico"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-8141-4154","authenticated-orcid":false,"given":"Kevin A.","family":"Romero-Sedglach","sequence":"additional","affiliation":[{"name":"Departamento de Qu\u00edmica, Centro de Investigaci\u00f3n y de Estudios Avanzados, Avenida IPN # 2508, 07360 Ciudad de M\u00e9xico, Mexico"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Erika C.","family":"V\u00e1zquez-Orta","sequence":"additional","affiliation":[{"name":"Departamento de Qu\u00edmica, Centro de Investigaci\u00f3n y de Estudios Avanzados, Avenida IPN # 2508, 07360 Ciudad de M\u00e9xico, Mexico"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-0936-7020","authenticated-orcid":false,"given":"Eusebio","family":"Juaristi","sequence":"additional","affiliation":[{"name":"Departamento de Qu\u00edmica, Centro de Investigaci\u00f3n y de Estudios Avanzados, Avenida IPN # 2508, 07360 Ciudad de M\u00e9xico, Mexico"},{"name":"El Colegio Nacional, Luis Gonz\u00e1lez Obreg\u00f3n # 23, Centro Hist\u00f3rico, 06020 Ciudad de M\u00e9xico, Mexico"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"1968","published-online":{"date-parts":[[2020,10,3]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"2395","DOI":"10.1021\/ja994280y","article-title":"Proline-Catalyzed Direct Asymmetric Aldol Reactions","volume":"122","author":"List","year":"2000","journal-title":"J. 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