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One-Pot, Two-Step Protocol for the Catalytic Asymmetric Synthesis of Optically Active N,O- and O,O-Acetals

Authors

  • M. Fatih Polat,

    1. KTH Royal Institute of Technology, School of Chemistry, Department of Chemistry, Organic Chemistry, Teknikringen 30, 100 44 Stockholm (Sweden)
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  • Lara Hettmanczyk,

    1. KTH Royal Institute of Technology, School of Chemistry, Department of Chemistry, Organic Chemistry, Teknikringen 30, 100 44 Stockholm (Sweden)
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  • Dr. Wei Zhang,

    1. KTH Royal Institute of Technology, School of Chemistry, Department of Chemistry, Organic Chemistry, Teknikringen 30, 100 44 Stockholm (Sweden)
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  • Dr. Zoltan Szabo,

    1. KTH Royal Institute of Technology, School of Chemistry, Department of Chemistry, Organic Chemistry, Teknikringen 30, 100 44 Stockholm (Sweden)
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  • Dr. Johan Franzén

    Corresponding author
    1. KTH Royal Institute of Technology, School of Chemistry, Department of Chemistry, Organic Chemistry, Teknikringen 30, 100 44 Stockholm (Sweden)
    • KTH Royal Institute of Technology, School of Chemistry, Department of Chemistry, Organic Chemistry, Teknikringen 30, 100 44 Stockholm (Sweden)
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Abstract

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N,O problem: An asymmetric catalytic one-pot N,O- and O,O-acetalization cascade is presented. This strategy is based on catalytic asymmetric conjugate addition and subsequent acid-catalyzed acetal formation that allows efficient and fast construction of functionalized dioxabicyclo- and oxaazabicyclo[3.3.1]nonane structures that are important motifs in several natural products and pharmaceutically interesting compounds.

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