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Enzyme-like Control of Carbocation Deprotonation Regioselectivity in Supramolecular Catalysis of the Nazarov Cyclization

Authors

  • Courtney J. Hastings,

    1. Department of Chemistry, University of California, Berkeley, Berkeley, CA 94720-1416 (USA)
    2. Lawrence Berkeley National Laboratory, 1 Cyclotron Road, Berkeley, CA 94720 (USA)
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  • Mikael P. Backlund,

    1. Department of Chemistry, University of California, Berkeley, Berkeley, CA 94720-1416 (USA)
    2. Lawrence Berkeley National Laboratory, 1 Cyclotron Road, Berkeley, CA 94720 (USA)
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  • Prof. Robert G. Bergman,

    Corresponding author
    1. Department of Chemistry, University of California, Berkeley, Berkeley, CA 94720-1416 (USA)
    2. Lawrence Berkeley National Laboratory, 1 Cyclotron Road, Berkeley, CA 94720 (USA)
    • Department of Chemistry, University of California, Berkeley, Berkeley, CA 94720-1416 (USA)
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  • Prof. Kenneth N. Raymond

    Corresponding author
    1. Department of Chemistry, University of California, Berkeley, Berkeley, CA 94720-1416 (USA)
    2. Lawrence Berkeley National Laboratory, 1 Cyclotron Road, Berkeley, CA 94720 (USA)
    • Department of Chemistry, University of California, Berkeley, Berkeley, CA 94720-1416 (USA)
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  • This work was supported by the Director of the Office of Energy Research, Office of Basic Energy Sciences, Chemical Sciences Division of the U.S. Department of Energy under Contract DE-AC02-05CH11231 and through a fellowship from Chevron (to C.J.H.).

Abstract

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Die kinetisch kontrollierte, regioselektive Deprotonierung von Cyclopentenylkationen wird durch Verkapselung mit einem Metall-Ligand-Aggregat vermittelt. Die Regiochemie des Deprotonierungsschritts bestimmt, welches der beiden möglichen Produkte gebildet wird. Feine Unterschied in der Stereochemie des Kations kehren zudem die Selektivität des Prozesses um (siehe Schema).

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