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Keywords:

  • cyclization;
  • Diels–Alder reaction;
  • Prins-type reaction;
  • silanes;
  • synthetic methods

Abstract

Thumbnail image of graphical abstract

Double or nothing: The title reaction converts a range of aromatic aldehydes and allenylmethyl/allyl silanes into 1,6-dioxecane derivatives in good to excellent yields (see scheme; Ar=aryl, Tf=triflate, THF=tetrahydrofuran, TMS=trimethylsilyl). In addition, the bisdiene product has been transformed into the corresponding tricyclic compound through a Diels–Alder reaction.