Organocatalytic Strategies for the Construction of Optically Active Imidazoles, Oxazoles, and Thiazoles

Authors

  • Dr. Łukasz Albrecht,

    1. Center for Catalysis, Department of Chemistry, Aarhus University, 8000 Aarhus C (Denmark), Fax: (+45) 8619-6199
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  • Lars Krogager Ransborg,

    1. Center for Catalysis, Department of Chemistry, Aarhus University, 8000 Aarhus C (Denmark), Fax: (+45) 8619-6199
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  • Dr. Anna Albrecht,

    1. Center for Catalysis, Department of Chemistry, Aarhus University, 8000 Aarhus C (Denmark), Fax: (+45) 8619-6199
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  • Lennart Lykke,

    1. Center for Catalysis, Department of Chemistry, Aarhus University, 8000 Aarhus C (Denmark), Fax: (+45) 8619-6199
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  • Prof. Dr. Karl Anker Jørgensen

    Corresponding author
    1. Center for Catalysis, Department of Chemistry, Aarhus University, 8000 Aarhus C (Denmark), Fax: (+45) 8619-6199
    • Center for Catalysis, Department of Chemistry, Aarhus University, 8000 Aarhus C (Denmark), Fax: (+45) 8619-6199
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Abstract

This study demonstrates the first enantioselective synthesis of hydroxyalkyl- and aminoalkyl-substituted imidazoles, oxazoles, and thiazoles. The approach developed utilizes a highly effective one-pot reaction cascade that consists of either an organocatalytic epoxidation or aziridination of α,β-unsaturated aldehydes coupled with a [3+2]-annulation, in which amidines, ureas, or thioureas act as effective 1,3-dinucleophilic species. The methodology described benefits from low catalyst loadings, commercially and readily available starting materials, and mild reaction conditions.

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