Rhodium-catalyzed asymmetric arylation of N-(tert-butanesulfinyl)imines with sodium tetraarylborates

J Org Chem. 2012 Jan 20;77(2):1095-100. doi: 10.1021/jo2024224. Epub 2012 Jan 3.

Abstract

A diastereoselective rhodium-catalyzed arylation of N-(tert-butanesulfinyl)imines with sodium tetraarylborates is described. This method is general for constructing various chiral α-branched amines and 2-substituted pyrrolidines with high diastereoselectivity. A practical asymmetric approach to access chiral amines has been developed involving the use of air-stable Rh catalysts and reagents and in the absence of an external ligand.

MeSH terms

  • Amines / chemical synthesis*
  • Amines / chemistry
  • Borates / chemical synthesis*
  • Borates / chemistry
  • Catalysis
  • Chemistry Techniques, Synthetic*
  • Magnetic Resonance Spectroscopy
  • Molecular Structure
  • Pyrrolidines / chemical synthesis
  • Pyrrolidines / chemistry
  • Rhodium / chemistry*
  • Stereoisomerism

Substances

  • Amines
  • Borates
  • Pyrrolidines
  • Rhodium