Highly Enantioselective Intermolecular Stetter Reaction of Simple Acrylates: Synthesis of α-Chiral γ-Ketoesters

Authors

  • Nathalie E. Wurz,

    1. Westfälische Wilhelms-Universität Münster, Organisch-Chemisches Institut, Corrensstrasse 40, 48149 Münster (Germany), Fax: (+49) 251-83-33202
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  • Dr. Constantin G. Daniliuc,

    1. Westfälische Wilhelms-Universität Münster, Organisch-Chemisches Institut, Corrensstrasse 40, 48149 Münster (Germany), Fax: (+49) 251-83-33202
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  • Prof. Dr. Frank Glorius

    Corresponding author
    1. Westfälische Wilhelms-Universität Münster, Organisch-Chemisches Institut, Corrensstrasse 40, 48149 Münster (Germany), Fax: (+49) 251-83-33202
    • Westfälische Wilhelms-Universität Münster, Organisch-Chemisches Institut, Corrensstrasse 40, 48149 Münster (Germany), Fax: (+49) 251-83-33202===

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Abstract

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Simple Stetter: A novel N-heterocyclic carbene (NHC) was designed by combining an electron-rich 2,6-dimethoxy substituent and an underestimated yet promising chiral motif. With this NHC in hand, a highly enantioselective intermolecular Stetter reaction of simple acrylates was developed, yielding versatile α-chiral γ-ketoesters. This represents the first catalytic asymmetric route towards these valuable compounds (see scheme).

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