A tandem isomerization/prins strategy: iridium(III)/Brønsted acid cooperative catalysis

Angew Chem Int Ed Engl. 2013 Dec 2;52(49):12910-4. doi: 10.1002/anie.201306462. Epub 2013 Nov 11.

Abstract

Working together: A mild and efficient isomerization/protonation sequence generates pyran-fused indoles by cooperative catalysis between cationic iridium(III) and Bi(OTf)3 . Three distinct cyclization manifolds lead to the corresponding bioactive scaffolds in good yields. In addition, N-substituted indoles can be synthesized enantioselectively in the presence of a chiral phosphate.

Keywords: bismuth; cooperative catalysis; cyclization; heterocycles; synthetic methods.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, Non-U.S. Gov't

MeSH terms

  • Catalysis
  • Coordination Complexes / chemistry*
  • Cyclization
  • Indoles / chemical synthesis*
  • Iridium / chemistry*
  • Isomerism
  • Mesylates / chemistry
  • Molecular Structure
  • Phosphoric Acids / chemistry
  • Pyrans / chemical synthesis
  • Stereoisomerism

Substances

  • Coordination Complexes
  • Indoles
  • Mesylates
  • Phosphoric Acids
  • Pyrans
  • Iridium
  • Bi(OTf)3
  • phosphoric acid