Catalytic Asymmetric Synthesis of Trifluoromethylated γ-Amino Acids through the Umpolung Addition of Trifluoromethyl Imines to Carboxylic Acid Derivatives

Angew Chem Int Ed Engl. 2018 Feb 19;57(8):2233-2237. doi: 10.1002/anie.201710915. Epub 2018 Jan 18.

Abstract

Novel cinchona alkaloid derived chiral phase-transfer catalysts enabled the highly chemo-, regio-, diastereo-, and enantioselective umpolung addition of trifluoromethyl imines to α,β-unsaturated N-acyl pyrroles. With a catalyst loading ranging from 0.2 to 5.0 mol %, this new catalytic asymmetric transformation provides facile and high-yielding access to highly enantiomerically enriched chiral trifluoromethylated γ-amino acids and γ-lactams.

Keywords: C−C bond formation; amino acids; asymmetric catalysis; phase-transfer catalysis; umpolung.

Publication types

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

MeSH terms

  • Amino Acids / chemical synthesis
  • Amino Acids / chemistry*
  • Carboxylic Acids / chemistry*
  • Catalysis
  • Cinchona Alkaloids / chemical synthesis
  • Cinchona Alkaloids / chemistry
  • Crystallography, X-Ray
  • Imines / chemistry*
  • Lactams / chemical synthesis
  • Lactams / chemistry
  • Molecular Conformation
  • Pyrroles / chemistry
  • Stereoisomerism

Substances

  • Amino Acids
  • Carboxylic Acids
  • Cinchona Alkaloids
  • Imines
  • Lactams
  • Pyrroles