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Palladium-Catalyzed Oxidative Cascade Carbonylative Spirolactonization 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 Organic Chemistry.
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Number of Authors: 5
2017 (English)In: Angewandte Chemie International Edition, ISSN 1433-7851, E-ISSN 1521-3773, Vol. 56, no 12, 3221-3225 p.Article in journal (Refereed) Published
Abstract [en]

A highly selective palladium-catalyzed oxidative carbonylation/carbocyclization/alkoxycarbonylation of enallenols to afford spirolactones bearing an all-carbon quaternary center was developed. This transformation involves the overall formation of three C-C bonds and one C-O bond through a cascade insertion of carbon monoxide (CO), an olefin, and CO. Preliminary experiments on chiral anion-induced enantioselective carbonylation/carbocyclization of enallenols afforded spirolactones with moderate enantioselectivity.

Place, publisher, year, edition, pages
2017. Vol. 56, no 12, 3221-3225 p.
Keyword [en]
carbocyclization, enallenols, oxidation, palladium, spirolactones
National Category
Organic Chemistry
Identifiers
URN: urn:nbn:se:su:diva-142591DOI: 10.1002/anie.201612384ISI: 000397329300015PubMedID: 28211212OAI: oai:DiVA.org:su-142591DiVA: diva2:1092679
Available from: 2017-05-03 Created: 2017-05-03 Last updated: 2017-05-03Bibliographically approved

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Qiu, YouaiYang, BinBäckvall, Jan-E.
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