Formation of Quaternary Centers by Copper-Catalyzed Asymmetric Conjugate Addition of Alkylzirconium Reagents

Authors

  • Dr. Mireia Sidera,

    1. Department of Chemistry, Chemistry Research Laboratory, University of Oxford, 12 Mansfield Road, Oxford, OX1 3TA (UK)
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    • These authors contributed equally to this work.

  • Philippe M. C. Roth,

    1. Department of Chemistry, Chemistry Research Laboratory, University of Oxford, 12 Mansfield Road, Oxford, OX1 3TA (UK)
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    • These authors contributed equally to this work.

  • Rebecca M. Maksymowicz,

    1. Department of Chemistry, Chemistry Research Laboratory, University of Oxford, 12 Mansfield Road, Oxford, OX1 3TA (UK)
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  • Dr. Stephen P. Fletcher

    Corresponding author
    1. Department of Chemistry, Chemistry Research Laboratory, University of Oxford, 12 Mansfield Road, Oxford, OX1 3TA (UK)
    • Department of Chemistry, Chemistry Research Laboratory, University of Oxford, 12 Mansfield Road, Oxford, OX1 3TA (UK)
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  • The authors thank the EPSRC for generous support of this research in the form of a Career Acceleration Fellowship to S.F. (EP/H003711/1). We are grateful to Prof. A. Alexakis for GC analysis of 3 b and Dr. B. Odell for assistance with the NMR experiments.

Abstract

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Pure and simple: Alkylzirconocenes generated in situ from simple alkenes are used in highly enantioselective copper-catalyzed 1,4-addition reactions to trisubstituted cyclic enones to generate quaternary centers. These reactions operate at room temperature under a range of conditions and tolerate many functional groups. Cp=cyclopentadienyl, Tf=trifluoromethanesulfonyl.

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