Anion-Induced Enantioselective Cyclization of Diynamides to Pyrrolidines Catalyzed by Cationic Gold Complexes

Authors

  • Asmaa Kamal Mourad,

    1. Institute for Chemistry and Biochemistry, Freie Universität Berlin, Takustrasse 3, 14195 Berlin (Germany)
    2. Fayoum University, University Zone, Fayoum, 63514 (Egypt)
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  • Juliane Leutzow,

    1. Institute for Chemistry and Biochemistry, Freie Universität Berlin, Takustrasse 3, 14195 Berlin (Germany)
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  • Dr. Constantin Czekelius

    Corresponding author
    1. Institute for Chemistry and Biochemistry, Freie Universität Berlin, Takustrasse 3, 14195 Berlin (Germany)
    • Institute for Chemistry and Biochemistry, Freie Universität Berlin, Takustrasse 3, 14195 Berlin (Germany)
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  • This work was generously supported by the DFG in the context of the Emmy-Noether program (CZ 183/1). A.K.M. is grateful for a DAAD doctoral fellowship. We thank Dr. Roman Rüttinger for experimental work employing chiral phosphine ligands (Table 1).

Abstract

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Only chiral anions do the job! Optically active gold complexes derived from substituted binol hydrogen phosphate catalyze the desymmetrizing cyclization of 1,4-diynamides. This reaction provides access to synthetically useful, chiral methylene pyrrolidines with an all-carbon-substituted quaternary stereocenter.

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