Addition of Diethylzinc to Aromatic Aldehydes Catalyzed by Hydrolase

A novel application of hydrolase as catalyst for the addition of diethylzinc to aromatic aldehydes is reported. Optimum conditions were screened out. Under the optimum conditions (i.e., reaction at 40 °C using hyperthermophilice esterase APE1547, 4-Cl-benzaldehyde substrate, and trichloromethane solvent), this reaction provided optically active secondary alcohol with an enantiomeric excess up to 56% and a yield up to 78%. The possible mechanism was proposed based on experimental observations and molecular dynamics simulation. These observations extend the phenomenon of enzyme promiscuity.