Highly enantioselective proton-initiated polycyclization of polyenes.

Abstract

This report describes the synthesis of a range of chiral polycyclic molecules (tricyclic to pentacyclic) from achiral polyene precursors by enantioselective proton-initiated polycyclization promoted by the 1:1 complex of o,o'-dichloro-BINOL and SbCl(5). Excellent yields (ca. 90% per ring formed) and enantioselectivety (20:1 to 50:1) were obtained. The process is practical as well as efficient, because the chiral ligand is both readily prepared from R,R- or S,S-BINOL and easily recovered from the reaction mixture by extraction.

Authors

Surendra, Karavadhi; Corey, E J;

Keywords

  • Antimony/ chemistry
  • Catalysis
  • Cyclization
  • Naphthols/ chemistry
  • Polycyclic Aromatic Hydrocarbons/ chemical synthesis
  • Polycyclic Aromatic Hydrocarbons/ chemistry
  • Polyenes/ chemistry
  • Protons
  • Stereoisomerism

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