Copper-boxmi complexes as highly enantioselective catalysts for electrophilic trifluoromethylthiolations

Chemistry. 2014 Jan 3;20(1):93-7. doi: 10.1002/chem.201303641. Epub 2013 Dec 11.

Abstract

The enantioselective trifluoromethylthiolation of β-ketoesters using chiral copper-boxmi complexes as catalysts is reported. A number of α-SCF3-substituted β-ketoesters have been obtained with up to >99% enantiomeric excess (ee), and the trifluoromethylthiolated products were then transformed diastereoselectively to α-SCF3-β-hydroxyesters with two adjacent quaternary stereocenters.

Keywords: asymmetric catalysis; copper; pincer ligands; trifluoromethylthiolation; β-ketoesters.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Catalysis
  • Coordination Complexes / chemistry*
  • Copper / chemistry*
  • Crystallography, X-Ray
  • Esters
  • Iodobenzenes
  • Iodobenzoates / chemistry
  • Ketones / chemistry
  • Molecular Conformation
  • Stereoisomerism

Substances

  • Coordination Complexes
  • Esters
  • Iodobenzenes
  • Iodobenzoates
  • Ketones
  • o-iodoxybenzoic acid
  • Copper