High throughput screening and evolution of a library of ligands in asymmetric H-transfer reduction of acetophenone

Comb Chem High Throughput Screen. 2010 Jun;13(5):393-413. doi: 10.2174/138620710791292985.

Abstract

A library of 117 ligands was combined with three transition metals Ru, Rh and Ir and screened with three different operating conditions for the asymmetric H-transfer reduction of acetophenone into phenylethanol. The combinatorial approach was based on evolution of a first library containing 60 ligands. For the evolution, operators such as replication, regression, cross-over and mutation were used. The study was performed with a XYZ robot and fast chiral GC analysis. Over only 4 generations, the average targeted criterion, enantioselectivity, was increased from 20% to ca. 80% for the 4th generation. The best results provided enantiomeric excess up to 93%.

MeSH terms

  • Acetophenones / chemistry*
  • Combinatorial Chemistry Techniques
  • High-Throughput Screening Assays / methods*
  • Hydrogen / chemistry*
  • Ligands
  • Molecular Structure
  • Organometallic Compounds / analysis*
  • Organometallic Compounds / chemistry*
  • Oxidation-Reduction
  • Phenylethyl Alcohol / chemical synthesis
  • Phenylethyl Alcohol / chemistry
  • Reproducibility of Results
  • Stereoisomerism

Substances

  • Acetophenones
  • Ligands
  • Organometallic Compounds
  • Hydrogen
  • Phenylethyl Alcohol
  • acetophenone