The Acetal Concept: Regioselective Access to ortho,ortho-Diphenols via Dibenzo-1,3-dioxepines

Authors

  • Dr. Kye-Simeon Masters,

    Corresponding author
    1. Institute of Organic Chemistry (IOC), Karlsruhe Institute of Technology (KIT), Fritz-Haber-Weg 6, 76133 Karlsruhe (Germany)
    • Institute of Organic Chemistry (IOC), Karlsruhe Institute of Technology (KIT), Fritz-Haber-Weg 6, 76133 Karlsruhe (Germany)
    Search for more papers by this author
  • Prof. Dr. Stefan Bräse

    Corresponding author
    1. Institute of Organic Chemistry (IOC), Karlsruhe Institute of Technology (KIT), Fritz-Haber-Weg 6, 76133 Karlsruhe (Germany)
    2. Institute of Toxicology and Genetics (ITG), Karlsruhe Institute of Technology (KIT), Eggenstein-Leopoldshafen (Germany)
    • Institute of Organic Chemistry (IOC), Karlsruhe Institute of Technology (KIT), Fritz-Haber-Weg 6, 76133 Karlsruhe (Germany)
    Search for more papers by this author

  • K.-S.M. would like to thank the Alexander von Humboldt Foundation for generous funding and support, and the Bräse group for the fond memories.

Abstract

original image

Traditional methods are ill-suited for the synthesis of ortho,ortho-biphenols, a structural motif found in many polyphenolic natural products, as well as synthetically useful compounds such as the chiral ligands binol, vapol, and vanol. The new route consists of a radical-based reaction of an acetal-tethered biphenyl ether substrate and subsequent hydrolytic cleavage of the dibenzo-1,3-dioxepine intermediate.

Ancillary