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Diastereoselective Cyclobutenol Synthesis: A Heterogeneous Palladium-Catalyzed Oxidative Carbocyclization-Borylation of Enallenols
Stockholm University, Faculty of Science, Department of Organic Chemistry.
Stockholm University, Faculty of Science, Department of Organic Chemistry.
Stockholm University, Faculty of Science, Department of Organic Chemistry.
Stockholm University, Faculty of Science, Department of Materials and Environmental Chemistry (MMK).
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Number of Authors: 72019 (English)In: Chemistry - A European Journal, ISSN 0947-6539, E-ISSN 1521-3765, Vol. 25, no 1, p. 210-215Article in journal (Refereed) Published
Abstract [en]

A highly selective and efficient oxidative carbocyclization/borylation of enallenols catalyzed by palladium immobilized on amino-functionalized siliceous mesocellular foam (Pd-AmP-MCF) was developed for diastereoselective cyclobutenol synthesis. The heterogeneous palladium catalyst can be recovered and recycled without any observed loss of activity or selectivity. The high diastereoselectivity of the reaction is proposed to originate from a directing effect of the enallenol hydroxyl group. Optically pure cyclobutenol synthesis was achieved by the heterogeneous strategy by using chiral enallenol obtained from kinetic resolution.

Place, publisher, year, edition, pages
2019. Vol. 25, no 1, p. 210-215
Keywords [en]
cyclobutenols, diastereoselectivity, enallenols, heterogeneous catalysis, oxidative carbocyclization, palladium
National Category
Chemical Sciences
Identifiers
URN: urn:nbn:se:su:diva-165694DOI: 10.1002/chem.201805118ISI: 000454705500025PubMedID: 30307089OAI: oai:DiVA.org:su-165694DiVA, id: diva2:1285707
Available from: 2019-02-05 Created: 2019-02-05 Last updated: 2019-02-05Bibliographically approved

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Li, Man-BoPosevins, DanielsGustafson, Karl P. J.Tai, Cheuk-WaiQiu, YouaiBäckvall, Jan-E.
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Department of Organic ChemistryDepartment of Materials and Environmental Chemistry (MMK)
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