Ruthenium-catalyzed enantioselective carbon-carbon bond forming reaction via allenylidene-ene process: synthetic approach to chiral heterocycles such as chromane, thiochromane, and 1,2,3,4-tetrahydroquinoline derivatives

J Am Chem Soc. 2008 Aug 13;130(32):10498-9. doi: 10.1021/ja8038745. Epub 2008 Jul 22.

Abstract

Our previously disclosed ruthenium-catalyzed carbon-carbon bond forming reactions between propargylic alcohols and alkenes via an allenylidene-ene type pathway have been successfully applied to an enantioselective intramolecular cyclization for a variety of chiral heterocycles such as chromane, thiochromane, and 1,2,3,4-tetrahydroquinoline derivatives (up to 99% ee) by use of a suitable optically active diruthenium complex as a catalyst. The methodology described in this paper becomes a novel synthetic approach to chiral heterocycles, the structures of which are widely found in many natural and biologically active compounds.

MeSH terms

  • Carbon / chemistry
  • Catalysis
  • Chromans / chemical synthesis*
  • Chromans / chemistry
  • Quinolines*
  • Ruthenium / chemistry*
  • Stereoisomerism

Substances

  • Chromans
  • Quinolines
  • Carbon
  • Ruthenium