Enantioselective Merger of Aminocatalysis with π-Lewis Acid Metal Catalysis: Asymmetric Preparation of Carbo- and Heterocycles

Authors

  • Dr. Chandrasekaran Praveen,

    1. Chimie ParisTech, Laboratoire Charles Friedel, UMR CNRS 7223, 11, rue Pierre et Marie Curie, 75231 Paris Cedex 05 (France), Fax: (+33) 1-44071062
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  • Dr. Benjamin Montaignac,

    1. Chimie ParisTech, Laboratoire Charles Friedel, UMR CNRS 7223, 11, rue Pierre et Marie Curie, 75231 Paris Cedex 05 (France), Fax: (+33) 1-44071062
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  • Dr. Maxime R. Vitale,

    1. Chimie ParisTech, Laboratoire Charles Friedel, UMR CNRS 7223, 11, rue Pierre et Marie Curie, 75231 Paris Cedex 05 (France), Fax: (+33) 1-44071062
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  • Dr. Virginie Ratovelomanana-Vidal,

    Corresponding author
    1. Chimie ParisTech, Laboratoire Charles Friedel, UMR CNRS 7223, 11, rue Pierre et Marie Curie, 75231 Paris Cedex 05 (France), Fax: (+33) 1-44071062
    • Chimie ParisTech, Laboratoire Charles Friedel, UMR CNRS 7223, 11, rue Pierre et Marie Curie, 75231 Paris Cedex 05 (France), Fax: (+33) 1-44071062
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  • Dr. Véronique Michelet

    Corresponding author
    1. Chimie ParisTech, Laboratoire Charles Friedel, UMR CNRS 7223, 11, rue Pierre et Marie Curie, 75231 Paris Cedex 05 (France), Fax: (+33) 1-44071062
    • Chimie ParisTech, Laboratoire Charles Friedel, UMR CNRS 7223, 11, rue Pierre et Marie Curie, 75231 Paris Cedex 05 (France), Fax: (+33) 1-44071062
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Abstract

The metallo-organocatalyzed enantioselective synthesis of various five-membered carbo- and heterocyclic structures through the merger of aminocatalysis with the catalytic indium(III) or copper(I) activation of α-disubstituted formyl alkynes is described. The use of indium trichloride associated with the (R)-1,1′-bis-(2-naphthylamine) ligand led to encouraging results with up to 85:15 enantiomeric ratio. After a careful examination of several other strategies, the best synergic catalytic system, which combines a chiral copper(I) complex with cyclohexylamine, afforded the enantioselective preparations of cyclopentane, indane, and pyrrolidine scaffolds with moderate to excellent control of the all-carbon quaternary stereogenic centers created through such cyclization processes.

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