Rhodium-catalyzed enantioselective addition of boronic acids to N-benzylnicotinate salts

J Am Chem Soc. 2011 Mar 9;133(9):2878-80. doi: 10.1021/ja111540g. Epub 2011 Feb 10.

Abstract

The highly enantioselective catalytic asymmetric addition of aryl and alkenylboronic acids to N-benzylnicotinate salt 1 is described. The dihydropyridine 2 reaction products can be converted to synthetically useful piperidines. Application of the methodology to the preparation of enantioenriched quaternary chiral centers is also discussed.

MeSH terms

  • Boronic Acids / chemical synthesis
  • Boronic Acids / chemistry*
  • Catalysis
  • Molecular Structure
  • Nicotinic Acids / chemical synthesis
  • Nicotinic Acids / chemistry*
  • Rhodium / chemistry*
  • Salts / chemical synthesis
  • Salts / chemistry
  • Stereoisomerism

Substances

  • Boronic Acids
  • Nicotinic Acids
  • Salts
  • Rhodium
  • nicotinic acid benzyl ester