Highly diastereoselective synthesis of tetrahydropyridines by a C-H activation-cyclization-reduction cascade

J Am Chem Soc. 2012 Mar 7;134(9):4064-7. doi: 10.1021/ja2119833. Epub 2012 Feb 22.

Abstract

A versatile reaction cascade leading to highly substituted 1,2,3,6-tetrahydropyridines has been developed. It comprises rhodium(I)-catalyzed C-H activation-alkyne coupling followed by electrocyclization and subsequent acid/borohydride-promoted reduction. This one-pot procedure affords the target compounds in up to 95% yield with >95% diastereomeric purity.

Publication types

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

MeSH terms

  • Catalysis
  • Cyclization
  • Molecular Structure
  • Oxidation-Reduction
  • Pyridines / chemical synthesis*
  • Pyridines / chemistry
  • Rhodium / chemistry
  • Stereoisomerism

Substances

  • Pyridines
  • Rhodium