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Divergent Outcomes of Carbene Transfer Reactions from Dirhodium- and Copper-Based Catalysts Separately or in Combination

Authors

  • Dr. Xinfang Xu,

    1. Department of Chemistry and Biochemistry, University of Maryland, College Park, MD 20742 (USA)
    2. Institute of Drug Discovery and Development, East China Normal University, 3663 Zhongshan Bei Road, Shanghai 200062 (China)
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  • Prof. Wen-Hao Hu,

    1. Institute of Drug Discovery and Development, East China Normal University, 3663 Zhongshan Bei Road, Shanghai 200062 (China)
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  • Dr. Peter Y. Zavalij,

    1. Department of Chemistry and Biochemistry, University of Maryland, College Park, MD 20742 (USA)
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  • Prof. Michael P. Doyle

    Corresponding author
    1. Department of Chemistry and Biochemistry, University of Maryland, College Park, MD 20742 (USA)
    • Department of Chemistry and Biochemistry, University of Maryland, College Park, MD 20742 (USA)
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  • Support for this research to M.P.D. from the National Institutes of Health (GM 46503) and National Science Foundation (CHE-0748121) is gratefully acknowledged. W.H. thanks the National Science Foundation of China (20932003), and the MOST of China (2011CB808600).

Abstract

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Divergente Katalyse: Je nach separater oder kombinierter Verwendung von Kupfer- und Rhodiumkatalysatoren wird die Reaktion zwischen Vinyldiazoacetaten 1 und Cinnamaldehyden 2 umgelenkt: von einer formalen [4+3]-Cycloaddition (Epoxidierung mit anschließender Cope-Umlagerung), zur intramolekularen Cyclopropanierung bis hin zur Mukaiyama-Aldolreaktion. Die jeweiligen Reaktionen sind selektiv und liefern hohe Ausbeuten.

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