High throughput screening and evolution of a library of ligands in asymmetric H-transfer reduction of acetophenone.
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%.
Laboratoire de Génie des Procédés Catalytiques, CNRS-ESCPE Lyon, Villeurbanne, France.
Radwan
R
Abdallah
Pierre
P
Grenouillet
Nicolas
N
Vriamont
Olivier
O
Riant
Claude
C
de Bellefon
D000098:Acetophenones / Q000737:chemistry*; D020650:Combinatorial Chemistry Techniques; D057166:High-Throughput Screening Assays / Q000379:methods*; D006859:Hydrogen / Q000737:chemistry*; D008024:Ligands; D015394:Molecular Structure; D009942:Organometallic Compounds / Q000032:analysis* / Q000737:chemistry*; D010084:Oxidation-Reduction; D010626:Phenylethyl Alcohol / Q000138:chemical synthesis / Q000737:chemistry; D015203:Reproducibility of Results; D013237:Stereoisomerism
D000098:Acetophenones; D008024:Ligands; D009942:Organometallic Compounds; D006859:Hydrogen; D010626:Phenylethyl Alcohol; C038699:acetophenone