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Immobilization of Functionalized epi-Cinchonine Organocatalysts on Controlled Porous Glass-Beads: Applications in Batch and Continuous Flow
University of Evora, Portugal.
University of Evora, Portugal.
ChiraTecnics, Portugal.
Chiratecnics, Portugal.
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2022 (English)In: Synlett: Accounts and Rapid Communications in Synthetic Organic Chemistry, ISSN 0936-5214, E-ISSN 1437-2096, Vol. 33, no 17, p. 1756-1762Article in journal (Refereed) Published
Abstract [en]

A well-known Squaramide-Cinchonine organocatalyst was immobilized in a controlled way onto three types of commercial porous glass beads EziGTM (EziG OPAL, EziG Amber and EziG Coral) and applied in asymmetric Michael reactions. The performance of the immobilized catalysts was evaluated under batch and continuous flow conditions showing promising results in both approaches. In batch reactions, 0.8 and 1.6 mol% of the immobilized cinchonine-squaramide provided the products with excellent yields (up to 99%) and enantioselectivities (up to 99% ee). These excellent results were also verified in the case of continuous flow reactions, where also 0.8 and 1.6 mol% of the catalyst immobilized onto the glass beads afforded the product with extraordinary yields (up to 99%) and very high enantioselectivities (up to 97% ee). The immobilized catalysts could be recycled (up to 7 cycles) using both approaches. 

Place, publisher, year, edition, pages
Georg Thieme Verlag , 2022. Vol. 33, no 17, p. 1756-1762
Keywords [en]
Batch reactions, Cinchona alkaloids, Continuous flow reactions, EziGTM, Immobilizations, Organocatalysis
National Category
Biochemistry and Molecular Biology
Identifiers
URN: urn:nbn:se:ri:diva-60064DOI: 10.1055/a-1916-4858Scopus ID: 2-s2.0-85135752027OAI: oai:DiVA.org:ri-60064DiVA, id: diva2:1692934
Available from: 2022-09-05 Created: 2022-09-05 Last updated: 2023-10-31Bibliographically approved

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Federsel, Hans-Jürgen

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