Designing N-Heterocyclic Carbenes: Simultaneous Enhancement of Reactivity and Enantioselectivity in the Asymmetric Hydroacylation of Cyclopropenes

Authors

  • Fan Liu,

    1. Organisch-Chemisches Institut, Westfälische Wilhelms-Universität Münster, Corrensstrasse 40, 48149 Münster (Germany)
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  • Dr. Xavier Bugaut,

    1. Organisch-Chemisches Institut, Westfälische Wilhelms-Universität Münster, Corrensstrasse 40, 48149 Münster (Germany)
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  • Michael Schedler,

    1. Organisch-Chemisches Institut, Westfälische Wilhelms-Universität Münster, Corrensstrasse 40, 48149 Münster (Germany)
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  • Dr. Roland Fröhlich,

    1. Organisch-Chemisches Institut, Westfälische Wilhelms-Universität Münster, Corrensstrasse 40, 48149 Münster (Germany)
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  • Prof. Dr. Frank Glorius

    Corresponding author
    1. Organisch-Chemisches Institut, Westfälische Wilhelms-Universität Münster, Corrensstrasse 40, 48149 Münster (Germany)
    • Organisch-Chemisches Institut, Westfälische Wilhelms-Universität Münster, Corrensstrasse 40, 48149 Münster (Germany)
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  • Generous financial support by the Deutsche Forschungsgemeinschaft (SFB 858) and the Deutscher Akademischer Austausch Dienst (F.L.) is gratefully acknowledged. The research of F.G. is supported by the Alfried Krupp Prize for Young University Teachers of the Alfried Krupp von Bohlen and Halbach Foundation. Dr. Isabel Piel is acknowledged for helpful discussion.

Abstract

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Faster, higher, stronger! The N-heterocyclic carbene (NHC) catalyzed diastereo- and enantioselective hydroacylation of cyclopropenes affords structurally valuable acylcyclopropanes. A new family of electron-rich, 2,6-dimethoxyphenyl-substituted NHCs induces excellent reactivity and enantioselectivity. Preliminary kinetic studies unambiguously demonstrated the superiority of this family of catalysts over known NHCs in this challenging transformation.

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