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Catalytic Enantioselective Claisen Rearrangements of O-Allyl β-Ketoesters

Authors

  • Christopher Uyeda,

    1. Department of Chemistry and Chemical Biology, Harvard University, 12 Oxford St., Cambridge, MA 02138 (USA), Fax: (+1) 617-496-1880
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  • Andreas R. Rötheli,

    1. Department of Chemistry and Chemical Biology, Harvard University, 12 Oxford St., Cambridge, MA 02138 (USA), Fax: (+1) 617-496-1880
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  • Prof. Dr. Eric N. Jacobsen

    Corresponding author
    1. Department of Chemistry and Chemical Biology, Harvard University, 12 Oxford St., Cambridge, MA 02138 (USA), Fax: (+1) 617-496-1880
    • Department of Chemistry and Chemical Biology, Harvard University, 12 Oxford St., Cambridge, MA 02138 (USA), Fax: (+1) 617-496-1880
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  • This work was supported by the NIH (GM-43214). We acknowledge Matthew Rienzo for experimental assistance and Dr. Richard Staples for X-ray analysis.

Abstract

original image

Ein chirales Guanidinium-Ion katalysiert die Titelreaktion mit 78–87 % ee (siehe Schema). Der pericyclische Verlauf des Prozesses ermöglicht die enantio- und diastereokontrollierte Bildung von Produkten mit vicinalen stereogenen Zentren.

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