Palladium-Catalyzed Oxidative Cascade Carbonylative Spirolactonization of Enallenols
Dr. Youai Qiu
Department of Organic Chemistry, Arrhenius Laboratory, Stockholm University, 10691 Stockholm, Sweden
Search for more papers by this authorBin Yang
Department of Organic Chemistry, Arrhenius Laboratory, Stockholm University, 10691 Stockholm, Sweden
Search for more papers by this authorDr. Tuo Jiang
Department of Organic Chemistry, Arrhenius Laboratory, Stockholm University, 10691 Stockholm, Sweden
Search for more papers by this authorDr. Can Zhu
Department of Organic Chemistry, Arrhenius Laboratory, Stockholm University, 10691 Stockholm, Sweden
Search for more papers by this authorCorresponding Author
Prof. Dr. Jan-E. Bäckvall
Department of Organic Chemistry, Arrhenius Laboratory, Stockholm University, 10691 Stockholm, Sweden
Search for more papers by this authorDr. Youai Qiu
Department of Organic Chemistry, Arrhenius Laboratory, Stockholm University, 10691 Stockholm, Sweden
Search for more papers by this authorBin Yang
Department of Organic Chemistry, Arrhenius Laboratory, Stockholm University, 10691 Stockholm, Sweden
Search for more papers by this authorDr. Tuo Jiang
Department of Organic Chemistry, Arrhenius Laboratory, Stockholm University, 10691 Stockholm, Sweden
Search for more papers by this authorDr. Can Zhu
Department of Organic Chemistry, Arrhenius Laboratory, Stockholm University, 10691 Stockholm, Sweden
Search for more papers by this authorCorresponding Author
Prof. Dr. Jan-E. Bäckvall
Department of Organic Chemistry, Arrhenius Laboratory, Stockholm University, 10691 Stockholm, Sweden
Search for more papers by this authorGraphical Abstract
All together now: A highly selective cascade reaction for C−C/C−O bond formation through palladium-catalyzed oxidative carbonylation/carbocyclization/alkoxycarbonylation of enallenols was developed, affording spirolactones bearing an all-carbon quaternary center. Preliminary attempts to obtain enantioselectivity in the carbonylative carbocyclization revealed that the VAPOL-type chiral phosphoric acid serves as a good anionic co-catalyst in this transformation.
Abstract
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.
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- 23For details of kinetic isotope effect study, see the Supporting Information.
