α,β-Divinyl tetrahydropyrroles as chiral chain diene ligands in rhodium(I)-catalyzed enantioselective conjugated additions

Org Lett. 2011 Mar 4;13(5):1122-5. doi: 10.1021/ol103152t. Epub 2011 Feb 10.

Abstract

A series of α,β-divinyl tetrahydropyrroles, synthesized by asymmetric allylic C-H bond activation/conjugated diene addition reaction of ene-2-dienes, were found to be very efficient chiral chain diene ligands in the rhodium-catalyzed conjugated addition of organoboronic acids to various α,β-unsaturated compounds, achieving the desired chiral adducts with good to excellent yields and ee values.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkadienes / chemical synthesis*
  • Alkadienes / chemistry
  • Catalysis
  • Combinatorial Chemistry Techniques
  • Ligands
  • Molecular Structure
  • Pyrroles / chemical synthesis*
  • Pyrroles / chemistry
  • Rhodium / chemistry*
  • Stereoisomerism

Substances

  • Alkadienes
  • Ligands
  • Pyrroles
  • Rhodium